AU2004220327B2 - Pyridyloxymethyl and benzisoxazole azabicyclic derivatives - Google Patents
Pyridyloxymethyl and benzisoxazole azabicyclic derivatives Download PDFInfo
- Publication number
- AU2004220327B2 AU2004220327B2 AU2004220327A AU2004220327A AU2004220327B2 AU 2004220327 B2 AU2004220327 B2 AU 2004220327B2 AU 2004220327 A AU2004220327 A AU 2004220327A AU 2004220327 A AU2004220327 A AU 2004220327A AU 2004220327 B2 AU2004220327 B2 AU 2004220327B2
- Authority
- AU
- Australia
- Prior art keywords
- octahydro
- benzo
- ylmethyl
- pyridin
- trans
- 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.)
- Ceased
Links
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 239
- 238000000034 method Methods 0.000 claims description 54
- 150000003839 salts Chemical class 0.000 claims description 54
- -1 pyrrolidin-1-ylmethyl-pyridin-2-yloxymethyl Chemical group 0.000 claims description 47
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- 239000000203 mixture Substances 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 25
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 24
- 208000035475 disorder Diseases 0.000 claims description 23
- 206010012289 Dementia Diseases 0.000 claims description 18
- 208000028017 Psychotic disease Diseases 0.000 claims description 18
- 201000000980 schizophrenia Diseases 0.000 claims description 18
- GXWNSJYVSIJRLS-UHFFFAOYSA-N 6-bromo-8-methylimidazo[1,2-a]pyrazine Chemical compound CC1=NC(Br)=CN2C=CN=C12 GXWNSJYVSIJRLS-UHFFFAOYSA-N 0.000 claims description 17
- 239000012453 solvate Substances 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 239000001301 oxygen Substances 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
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- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 claims description 8
- 208000018737 Parkinson disease Diseases 0.000 claims description 8
- 125000002950 monocyclic group Chemical group 0.000 claims description 8
- 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 7
- ONHPOXROAPYCGT-UHFFFAOYSA-N 2,3,4,6,7,8,9,9a-octahydro-1h-pyrido[1,2-a]pyrazine Chemical compound C1CNCC2CCCCN21 ONHPOXROAPYCGT-UHFFFAOYSA-N 0.000 claims description 7
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
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- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 claims description 3
- 229950010883 phencyclidine Drugs 0.000 claims description 3
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- PJEAHOHAPYWSEB-UHFFFAOYSA-N 4h-pyrido[1,2-a]pyrazine Chemical compound C1=CC=CN2CC=NC=C21 PJEAHOHAPYWSEB-UHFFFAOYSA-N 0.000 claims description 2
- AXLOCHLTNQDFFS-BESJYZOMSA-N azastene Chemical compound C([C@H]1[C@@H]2CC[C@@]([C@]2(CC[C@@H]1[C@@]1(C)C2)C)(O)C)C=C1C(C)(C)C1=C2C=NO1 AXLOCHLTNQDFFS-BESJYZOMSA-N 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 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 2
- 241000218236 Cannabis Species 0.000 claims 2
- 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 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 300
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- 239000002904 solvent Substances 0.000 description 68
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
- 229910052938 sodium sulfate Inorganic materials 0.000 description 66
- 235000011152 sodium sulphate Nutrition 0.000 description 66
- 238000010898 silica gel chromatography Methods 0.000 description 60
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- 239000007858 starting material Substances 0.000 description 52
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- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 44
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 44
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 42
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 37
- 238000001816 cooling Methods 0.000 description 37
- 101150041968 CDC13 gene Proteins 0.000 description 36
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 description 36
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 36
- 239000011541 reaction mixture Substances 0.000 description 34
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 32
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 32
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 21
- 239000007787 solid Substances 0.000 description 21
- SKCNYHLTRZIINA-UHFFFAOYSA-N 2-chloro-5-(chloromethyl)pyridine Chemical compound ClCC1=CC=C(Cl)N=C1 SKCNYHLTRZIINA-UHFFFAOYSA-N 0.000 description 20
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- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 15
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Classifications
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Landscapes
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Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2010203303A AU2010203303A1 (en) | 2003-03-12 | 2010-07-23 | Pyridyloxymethyl and benzisoxazole azabicyclic derivatives |
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| US45392503P | 2003-03-12 | 2003-03-12 | |
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| PCT/IB2004/000499 WO2004081007A1 (en) | 2003-03-12 | 2004-02-23 | Pyridyloxymethyl and benzisoxazole azabicyclic derivatives |
Related Child Applications (1)
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| AU2010203303A Division AU2010203303A1 (en) | 2003-03-12 | 2010-07-23 | Pyridyloxymethyl and benzisoxazole azabicyclic derivatives |
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| AU2004220327A1 AU2004220327A1 (en) | 2004-09-23 |
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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 |
| KR100872204B1 (ko) | 2003-10-15 | 2008-12-09 | 오에스아이 파마슈티컬스, 인코포레이티드 | 이미다조피라진 티로신 키나제 억제제 |
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