JP4489354B2 - スピロインデンおよびスピロインダン化合物類 - Google Patents
スピロインデンおよびスピロインダン化合物類 Download PDFInfo
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- JP4489354B2 JP4489354B2 JP2002582927A JP2002582927A JP4489354B2 JP 4489354 B2 JP4489354 B2 JP 4489354B2 JP 2002582927 A JP2002582927 A JP 2002582927A JP 2002582927 A JP2002582927 A JP 2002582927A JP 4489354 B2 JP4489354 B2 JP 4489354B2
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- JP
- Japan
- Prior art keywords
- spiro
- piperidine
- alkyl
- indane
- indene
- 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 83
- -1 cyclodecyl Chemical group 0.000 claims description 119
- 125000000217 alkyl group Chemical group 0.000 claims description 73
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 108010020615 nociceptin receptor Proteins 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 10
- 102000051367 mu Opioid Receptors Human genes 0.000 claims description 9
- 108020001612 μ-opioid receptors Proteins 0.000 claims description 8
- 230000000202 analgesic effect Effects 0.000 claims description 7
- 125000004043 oxo group Chemical group O=* 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 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 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- LNMOBTPIDPUKDV-UHFFFAOYSA-N 1'-(3,3-dimethyl-1,5-dioxaspiro[5.5]undecan-9-yl)spiro[1,2-dihydroindene-3,4'-piperidine] Chemical compound O1CC(C)(C)COC11CCC(N2CCC3(C4=CC=CC=C4CC3)CC2)CC1 LNMOBTPIDPUKDV-UHFFFAOYSA-N 0.000 claims description 3
- YJGQGVFLPGUOQS-UHFFFAOYSA-N 1'-(3,3-dimethyl-1,5-dioxaspiro[5.5]undecan-9-yl)spiro[indene-1,4'-piperidine] Chemical compound O1CC(C)(C)COC11CCC(N2CCC3(CC2)C2=CC=CC=C2C=C3)CC1 YJGQGVFLPGUOQS-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 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 3
- 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 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
- KRPSXNNVCBQCEC-UHFFFAOYSA-N 1'-(4-propylcyclohexyl)spiro[1,2-dihydroindene-3,4'-piperidine] Chemical compound C1CC(CCC)CCC1N1CCC2(C3=CC=CC=C3CC2)CC1 KRPSXNNVCBQCEC-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
- 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 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
- URGFMBOYZAXORX-UHFFFAOYSA-N 1'-cyclooctylspiro[indene-1,4'-piperidine] Chemical compound C1CC2(C3=CC=CC=C3C=C2)CCN1C1CCCCCCC1 URGFMBOYZAXORX-UHFFFAOYSA-N 0.000 claims description 3
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 230000036592 analgesia Effects 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
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 230000003796 beauty Effects 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 28
- 239000000203 mixture Substances 0.000 description 27
- 239000003112 inhibitor Substances 0.000 description 24
- 125000003118 aryl group Chemical group 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000003814 drug Substances 0.000 description 18
- 238000005160 1H NMR spectroscopy Methods 0.000 description 16
- 102000005962 receptors Human genes 0.000 description 16
- 108020003175 receptors Proteins 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- 125000000623 heterocyclic group Chemical group 0.000 description 14
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 13
- 125000001072 heteroaryl group Chemical group 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 description 13
- 239000002552 dosage form Substances 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 208000002193 Pain Diseases 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 150000002431 hydrogen Chemical group 0.000 description 10
- 239000000556 agonist Substances 0.000 description 9
- 125000003342 alkenyl group Chemical group 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 229940079593 drug Drugs 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 239000012528 membrane Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 125000003282 alkyl amino group Chemical group 0.000 description 7
- 239000005557 antagonist Substances 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 238000004440 column chromatography Methods 0.000 description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 7
- 239000003607 modifier Substances 0.000 description 7
- 239000006186 oral dosage form Substances 0.000 description 7
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 108010050904 Interferons Proteins 0.000 description 6
- 102000014150 Interferons Human genes 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 6
- 125000002619 bicyclic group Chemical group 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 229940079322 interferon Drugs 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 125000002950 monocyclic group Chemical group 0.000 description 6
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
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- 229940124597 therapeutic agent Drugs 0.000 description 6
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- 208000000094 Chronic Pain Diseases 0.000 description 5
- 108090000137 Opioid Receptors Proteins 0.000 description 5
- 101100244562 Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1) oprD gene Proteins 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000000730 antalgic agent Substances 0.000 description 5
- 239000001961 anticonvulsive agent Substances 0.000 description 5
- 108700023159 delta Opioid Receptors Proteins 0.000 description 5
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- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 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 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
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Landscapes
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|---|---|---|---|
| US28467001P | 2001-04-18 | 2001-04-18 | |
| PCT/US2002/012357 WO2002085354A1 (en) | 2001-04-18 | 2002-04-18 | Spiroindene and spiroindane compounds |
Publications (3)
| Publication Number | Publication Date |
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| JP2004532223A JP2004532223A (ja) | 2004-10-21 |
| JP2004532223A5 JP2004532223A5 (enExample) | 2005-12-22 |
| JP4489354B2 true JP4489354B2 (ja) | 2010-06-23 |
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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 |
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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
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| Publication number | Publication date |
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| 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 |
| CA2443938C (en) | 2010-06-22 |
| 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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