JP3910627B2 - ピリジルオキシメチルおよびベンゾイソオキサゾールのアザビシクロ環の誘導体 - Google Patents
ピリジルオキシメチルおよびベンゾイソオキサゾールのアザビシクロ環の誘導体 Download PDFInfo
- Publication number
- JP3910627B2 JP3910627B2 JP2006506261A JP2006506261A JP3910627B2 JP 3910627 B2 JP3910627 B2 JP 3910627B2 JP 2006506261 A JP2006506261 A JP 2006506261A JP 2006506261 A JP2006506261 A JP 2006506261A JP 3910627 B2 JP3910627 B2 JP 3910627B2
- Authority
- JP
- Japan
- Prior art keywords
- octahydro
- benzo
- isoxazol
- pyrido
- ylmethyl
- 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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- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 253
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 135
- -1 hydroxy, amino Chemical group 0.000 claims description 102
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 36
- 239000001257 hydrogen Substances 0.000 claims description 36
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 24
- 229910052760 oxygen Inorganic materials 0.000 claims description 22
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 20
- 239000001301 oxygen Substances 0.000 claims description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 13
- 125000002950 monocyclic group Chemical group 0.000 claims description 13
- 229910052717 sulfur Chemical group 0.000 claims description 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 11
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 11
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
- 239000011593 sulfur Chemical group 0.000 claims description 10
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 9
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000003367 polycyclic group Chemical group 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- PJMUNJOFKTZCIW-UHFFFAOYSA-N 3-[7-[[5-(pyrrolidin-1-ylmethyl)pyridin-2-yl]oxymethyl]-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazin-1-yl]-1,2-oxazole Chemical compound O1N=C(C=C1)C1C2N(CCN1)CC(CC2)COC2=NC=C(C=C2)CN2CCCC2 PJMUNJOFKTZCIW-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 239000012453 solvate Substances 0.000 claims description 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 claims description 4
- GFNMLOFOXILWJE-UHFFFAOYSA-N 3-[7-[[6-(pyrrolidin-1-ylmethyl)pyridin-2-yl]oxymethyl]-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazin-1-yl]-1,2-oxazole Chemical compound O1N=C(C=C1)C1C2N(CCN1)CC(CC2)COC1=NC(=CC=C1)CN1CCCC1 GFNMLOFOXILWJE-UHFFFAOYSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- AMNSTJVLSCINFN-JCUDRXCFSA-N 3-[(7R,9aS)-7-[[6-[[(2S,5S)-2,5-dimethylpyrrolidin-1-yl]methyl]pyridin-2-yl]oxymethyl]-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-2-yl]-5-fluoro-1,2-benzoxazole Chemical compound C[C@@H]1N([C@H](CC1)C)CC1=CC=CC(=N1)OC[C@@H]1CC[C@@H]2N(CCN(C2)C2=NOC3=C2C=C(C=C3)F)C1 AMNSTJVLSCINFN-JCUDRXCFSA-N 0.000 claims description 3
- KETKNCJQPBIFRE-FUCAVZNHSA-N 3-[(7R,9aS)-7-[[6-[[(2S,6S)-2,6-dimethylpiperidin-1-yl]methyl]pyridin-2-yl]oxymethyl]-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-2-yl]-5-fluoro-1,2-benzoxazole Chemical compound C[C@@H]1N([C@H](CCC1)C)CC1=CC=CC(=N1)OC[C@@H]1CC[C@@H]2N(CCN(C2)C2=NOC3=C2C=C(C=C3)F)C1 KETKNCJQPBIFRE-FUCAVZNHSA-N 0.000 claims description 3
- GXAUMTXKKVKIJZ-UHFFFAOYSA-N 3-[7-[[5-(piperidin-1-ylmethyl)pyridin-2-yl]oxymethyl]-2,3,4,6,7,8,9,9a-octahydro-1h-pyrido[1,2-a]pyrazin-1-yl]-1,2-oxazole Chemical compound C1CC2C(C3=NOC=C3)NCCN2CC1COC(N=C1)=CC=C1CN1CCCCC1 GXAUMTXKKVKIJZ-UHFFFAOYSA-N 0.000 claims description 3
- MSOXFHMCXLIFRJ-UHFFFAOYSA-N 3-[7-[[5-[(2-methylaziridin-1-yl)methyl]pyridin-2-yl]oxymethyl]-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazin-1-yl]-1,2-oxazole Chemical compound O1N=C(C=C1)C1C2N(CCN1)CC(CC2)COC1=NC=C(C=C1)CN1C(C1)C MSOXFHMCXLIFRJ-UHFFFAOYSA-N 0.000 claims description 3
- YYWGUWVWUGWQPY-UHFFFAOYSA-N 3-[7-[[5-[(2-methylpyrrolidin-1-yl)methyl]pyridin-2-yl]oxymethyl]-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazin-1-yl]-1,2-oxazole Chemical compound O1N=C(C=C1)C1C2N(CCN1)CC(CC2)COC1=NC=C(C=C1)CN1C(CCC1)C YYWGUWVWUGWQPY-UHFFFAOYSA-N 0.000 claims description 3
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- FVCBUSCIOBOAAE-UHFFFAOYSA-N 3-[7-[[5-[(4-methyl-1,4-diazepan-1-yl)methyl]pyridin-2-yl]oxymethyl]-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazin-1-yl]-1,2-oxazole Chemical compound O1N=C(C=C1)C1C2N(CCN1)CC(CC2)COC2=NC=C(C=C2)CN2CCN(CCC2)C FVCBUSCIOBOAAE-UHFFFAOYSA-N 0.000 claims description 2
- YLWDZDORIQWYNS-UHFFFAOYSA-N 3-[7-[[5-[[2-(methoxymethyl)pyrrolidin-1-yl]methyl]pyridin-2-yl]oxymethyl]-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazin-1-yl]-1,2-oxazole Chemical compound O1N=C(C=C1)C1C2N(CCN1)CC(CC2)COC1=NC=C(C=C1)CN1C(CCC1)COC YLWDZDORIQWYNS-UHFFFAOYSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 3
- LPLFRMNZSFKRJA-UHFFFAOYSA-N 4-[[6-[[1-(1,2-oxazol-3-yl)-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazin-7-yl]methoxy]pyridin-2-yl]methyl]morpholine Chemical compound O1N=C(C=C1)C1C2N(CCN1)CC(CC2)COC1=NC(=CC=C1)CN1CCOCC1 LPLFRMNZSFKRJA-UHFFFAOYSA-N 0.000 claims 2
- YDOQLJXCEUEJNJ-UHFFFAOYSA-N 3-[7-[[5-(1,3-thiazolidin-3-ylmethyl)pyridin-2-yl]oxymethyl]-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazin-1-yl]-1,2-oxazole Chemical compound O1N=C(C=C1)C1C2N(CCN1)CC(CC2)COC1=NC=C(C=C1)CN1CSCC1 YDOQLJXCEUEJNJ-UHFFFAOYSA-N 0.000 claims 1
- PSCOJTKUFQSHFS-UHFFFAOYSA-N 3-[7-[[5-(imidazol-1-ylmethyl)pyridin-2-yl]oxymethyl]-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazin-1-yl]-1,2-oxazole Chemical compound O1N=C(C=C1)C1C2N(CCN1)CC(CC2)COC1=NC=C(C=C1)CN1C=NC=C1 PSCOJTKUFQSHFS-UHFFFAOYSA-N 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 301
- 239000000243 solution Substances 0.000 description 140
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Classifications
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Landscapes
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US45392503P | 2003-03-12 | 2003-03-12 | |
| PCT/IB2004/000499 WO2004081007A1 (en) | 2003-03-12 | 2004-02-23 | Pyridyloxymethyl and benzisoxazole azabicyclic derivatives |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| JP2006291545A Division JP2007051155A (ja) | 2003-03-12 | 2006-10-26 | ピリジルオキシメチルおよびベンゾイソオキサゾールのアザビシクロ環の誘導体 |
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| JP2006519830A JP2006519830A (ja) | 2006-08-31 |
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| JP2006291545A Pending JP2007051155A (ja) | 2003-03-12 | 2006-10-26 | ピリジルオキシメチルおよびベンゾイソオキサゾールのアザビシクロ環の誘導体 |
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| EC (1) | ECSP056011A (enExample) |
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| US6994726B2 (en) * | 2004-05-25 | 2006-02-07 | Calcitec, Inc. | Dual function prosthetic bone implant and method for preparing the same |
| ES2372694T3 (es) | 2003-10-15 | 2012-01-25 | OSI Pharmaceuticals, LLC | Inhibidores de tirosina cinasa de imidazo[1,5-a]pirazina. |
| BRPI0507250A (pt) * | 2004-01-29 | 2007-06-26 | Pfizer Prod Inc | combinações para tratar desordens do snc |
| MXPA06011423A (es) | 2004-04-02 | 2007-01-23 | Osi Pharm Inc | Inhibidores de proteina cinasa heterobiciclica sustituida en el anillo 6,6-biciclico. |
| MY139689A (en) | 2004-07-20 | 2009-10-30 | Osi Pharm Inc | Imidazotriazines as protein kinase inhibitors |
| CA2580042A1 (en) * | 2004-09-10 | 2006-03-16 | Pfizer Products Inc. | Methods of treating cognitive disorders using pyridyloxymethyl and benzisoxazole azabicyclic derivatives |
| US8575164B2 (en) * | 2005-12-19 | 2013-11-05 | OSI Pharmaceuticals, LLC | Combination cancer therapy |
| EP2250173A1 (en) * | 2008-01-18 | 2010-11-17 | OSI Pharmaceuticals, Inc. | Imidazopyrazinol derivatives for the treatment of cancers |
| ES2396613T3 (es) * | 2008-05-19 | 2013-02-22 | OSI Pharmaceuticals, LLC | Imidazopirazinas e imidazotriazinas sustituidas |
| EP2421837A1 (en) | 2009-04-20 | 2012-02-29 | OSI Pharmaceuticals, LLC | Preparation of c-pyrazine-methylamines |
| WO2010129740A1 (en) * | 2009-05-07 | 2010-11-11 | Osi Pharmaceuticals, Inc. | Use of osi-906 for treating adrenocortical carcinoma |
| JP2013540145A (ja) * | 2010-10-21 | 2013-10-31 | ウニベルシテート デス ザールランデス | コルチゾール依存性疾患の治療用の選択的ｃｙｐ１１ｂ１阻害剤 |
| US10154988B2 (en) | 2012-11-14 | 2018-12-18 | The Johns Hopkins University | Methods and compositions for treating schizophrenia |
| WO2016115282A1 (en) * | 2015-01-13 | 2016-07-21 | Vanderbilt University | Benzoisoxazole-substituted compounds as mglur4 allosteric potentiators, compositions, and methods of treating neurological dysfunction |
| US20170038184A1 (en) | 2015-08-06 | 2017-02-09 | Charles E. Ankner | Formulation delivery system |
| US9585867B2 (en) | 2015-08-06 | 2017-03-07 | Charles Everett Ankner | Cannabinod formulation for the sedation of a human or animal |
| WO2020183011A1 (en) | 2019-03-14 | 2020-09-17 | Institut Curie | Htr1d inhibitors and uses thereof in the treatment of cancer |
| EP4429465A1 (en) | 2021-11-10 | 2024-09-18 | Symrise AG | Compositions comprising trpm8 agonistic cooling agents |
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| WO1990008148A1 (en) | 1989-01-23 | 1990-07-26 | Pfizer Inc. | Bis-aza-bicyclic anxiolytic agents |
| US5167034A (en) * | 1990-06-18 | 1992-11-24 | International Business Machines Corporation | Data integrity for compaction devices |
| US5157034A (en) | 1991-02-27 | 1992-10-20 | Pfizer Inc. | Neuroleptic perhydro-1H-pyrido[1,2-a]pyrazines |
| ES2096099T3 (es) | 1991-09-25 | 1997-03-01 | Pfizer | Perhidro-1h-pirido(1,2,a)pirazinas 2-sustituidas neurolepticas. |
| WO1993025552A1 (en) | 1992-06-16 | 1993-12-23 | Pfizer Inc. | Process and intermediates for bis-aza-bicyclic anxiolytic agents |
| WO1996010570A1 (en) | 1994-09-30 | 1996-04-11 | Pfizer Inc. | NEUROLEPTIC 2,7-DISUBSTITUTED PERHYDRO-1H-PYRIDO[1,2-a]PYRAZINES |
| KR100589872B1 (ko) | 1997-05-30 | 2006-06-15 | 뉴로서치 에이/에스 | 8-아자비사이클로(3,2,1)옥트-2-엔 유도체 및 이의 제조방법 |
| PA8469101A1 (es) | 1998-04-09 | 2000-09-29 | Pfizer Prod Inc | Ligandos azabiciclicos de receptores 5ht1 |
| PT1114028E (pt) | 1998-08-26 | 2007-02-28 | Aventis Pharma Ltd | Aza-biciclos moduladores da inibição da adesão celular |
| CZ2001959A3 (cs) | 1998-09-18 | 2001-12-12 | Basf Aktiengesellschaft | 4-Aminopyrrolopyrimidiny jako inhibitory kinasy |
| NZ510588A (en) | 1998-09-18 | 2003-08-29 | Abbott Gmbh & Co | Pyrrolopyrimidines as protein kinase inhibitors |
| UA62015C2 (en) * | 1998-12-28 | 2003-12-15 | Pfizer Prod Inc | Benzoizoxazol derivatives, a pharmaceutical composition (variants) based thereon (variants) and a method for treatment (variants) |
| TR200102817T2 (tr) | 1999-03-12 | 2002-05-21 | Boehringer Ingelheim Pharmaceuticals, Inc. | Antiinflamatuar ajanlar olarak faydalı bileşikler |
| EP1177792A3 (en) * | 2000-07-27 | 2002-10-23 | Pfizer Products Inc. | Dopamine D4 Ligands for the treatment of novelty-seeking disorders |
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