JP2008530011A5 - - Google Patents
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- JP2008530011A5 JP2008530011A5 JP2007554205A JP2007554205A JP2008530011A5 JP 2008530011 A5 JP2008530011 A5 JP 2008530011A5 JP 2007554205 A JP2007554205 A JP 2007554205A JP 2007554205 A JP2007554205 A JP 2007554205A JP 2008530011 A5 JP2008530011 A5 JP 2008530011A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- pyridin
- pyrazol
- alkyl
- oxime
- 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.)
- Pending
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- 150000001875 compounds Chemical class 0.000 claims 77
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 63
- 125000000623 heterocyclic group Chemical group 0.000 claims 49
- 125000000217 alkyl group Chemical group 0.000 claims 45
- 125000003118 aryl group Chemical group 0.000 claims 32
- -1 carbocycle Chemical group 0.000 claims 30
- 125000004452 carbocyclyl group Chemical group 0.000 claims 27
- 125000003342 alkenyl group Chemical group 0.000 claims 18
- 125000000304 alkynyl group Chemical group 0.000 claims 16
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 13
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 239000000203 mixture Substances 0.000 claims 13
- 206010028980 Neoplasm Diseases 0.000 claims 11
- 125000004429 atom Chemical group 0.000 claims 11
- 201000011510 cancer Diseases 0.000 claims 10
- 229910052760 oxygen Inorganic materials 0.000 claims 10
- 229910052799 carbon Inorganic materials 0.000 claims 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- 125000005842 heteroatom Chemical group 0.000 claims 8
- 229910052757 nitrogen Inorganic materials 0.000 claims 8
- 150000003951 lactams Chemical class 0.000 claims 7
- 150000002596 lactones Chemical class 0.000 claims 7
- 238000000034 method Methods 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 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 claims 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 6
- 239000003814 drug Substances 0.000 claims 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 229940124597 therapeutic agent Drugs 0.000 claims 5
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 230000000069 prophylactic effect Effects 0.000 claims 4
- 125000006239 protecting group Chemical group 0.000 claims 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 4
- 238000002560 therapeutic procedure Methods 0.000 claims 4
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 4
- 241000124008 Mammalia Species 0.000 claims 3
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims 3
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims 3
- 230000004770 neurodegeneration Effects 0.000 claims 3
- 208000015122 neurodegenerative disease Diseases 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 3
- 125000005942 tetrahydropyridyl group Chemical group 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims 2
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- JQGPBDSMTHZOMO-UHFFFAOYSA-N OBO.C=1C=NNC=1 Chemical class OBO.C=1C=NNC=1 JQGPBDSMTHZOMO-UHFFFAOYSA-N 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 208000015634 Rectal Neoplasms Diseases 0.000 claims 2
- 235000010290 biphenyl Nutrition 0.000 claims 2
- 239000004305 biphenyl Substances 0.000 claims 2
- 210000004027 cell Anatomy 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 125000005057 dihydrothienyl group Chemical group S1C(CC=C1)* 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 208000019423 liver disease Diseases 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 210000000214 mouth Anatomy 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 206010038038 rectal cancer Diseases 0.000 claims 2
- 201000001275 rectum cancer Diseases 0.000 claims 2
- 208000037803 restenosis Diseases 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 2
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 claims 1
- IZQZVLNYVZCOPX-UHFFFAOYSA-N 2-[2-[4-(1-hydroxyimino-2,3-dihydroinden-5-yl)-3-pyridin-4-ylpyrazol-1-yl]ethylamino]ethanol Chemical compound N=1N(CCNCCO)C=C(C=2C=C3CCC(C3=CC=2)=NO)C=1C1=CC=NC=C1 IZQZVLNYVZCOPX-UHFFFAOYSA-N 0.000 claims 1
- FKWQBUGNQFJRGV-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-3-pyridin-4-ylpyrazol-1-yl]ethanol Chemical compound N=1N(CCO)C=C(C=2C=C3OCOC3=CC=2)C=1C1=CC=NC=C1 FKWQBUGNQFJRGV-UHFFFAOYSA-N 0.000 claims 1
- MJESHTQDIHRJJJ-UHFFFAOYSA-N 2-[4-(1-amino-2,3-dihydro-1h-inden-5-yl)-3-pyridin-4-ylpyrazol-1-yl]ethanol Chemical compound C=1C=C2C(N)CCC2=CC=1C1=CN(CCO)N=C1C1=CC=NC=C1 MJESHTQDIHRJJJ-UHFFFAOYSA-N 0.000 claims 1
- IEPBUTPKELRFKK-UHFFFAOYSA-N 2-[4-(1-amino-2,3-dihydro-1h-inden-5-yl)-5-pyridin-4-ylpyrazol-1-yl]ethanol Chemical compound C=1C=C2C(N)CCC2=CC=1C=1C=NN(CCO)C=1C1=CC=NC=C1 IEPBUTPKELRFKK-UHFFFAOYSA-N 0.000 claims 1
- PKGNJPQGDHTVGY-UHFFFAOYSA-N 2-[4-(1-hydroxyimino-2,3-dihydroinden-5-yl)-3-pyridin-4-ylpyrazol-1-yl]pyridine-3-carbonitrile Chemical compound C=1C=C2C(=NO)CCC2=CC=1C1=CN(C=2C(=CC=CN=2)C#N)N=C1C1=CC=NC=C1 PKGNJPQGDHTVGY-UHFFFAOYSA-N 0.000 claims 1
- SQFQKKPNPXONBG-UHFFFAOYSA-N 2-[4-(1-hydroxyimino-2,3-dihydroinden-5-yl)-5-pyridin-4-ylpyrazol-1-yl]ethanol Chemical compound OCCN1N=CC(C=2C=C3CCC(C3=CC=2)=NO)=C1C1=CC=NC=C1 SQFQKKPNPXONBG-UHFFFAOYSA-N 0.000 claims 1
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 claims 1
- VATRAMGKPXJFAV-UHFFFAOYSA-N 3-[4-(1-hydroxyimino-2,3-dihydroinden-5-yl)-3-pyridin-4-ylpyrazol-1-yl]propane-1,2-diol Chemical compound N=1N(CC(O)CO)C=C(C=2C=C3CCC(C3=CC=2)=NO)C=1C1=CC=NC=C1 VATRAMGKPXJFAV-UHFFFAOYSA-N 0.000 claims 1
- RCBZCSONTXNSHW-UHFFFAOYSA-N 4-[1-piperidin-4-yl-4-[6-(1h-pyrazol-5-yl)-2,4,5,6-tetrahydro-1h-inden-5-yl]pyrazol-3-yl]pyridine Chemical compound C1C2=CCCC2=CC(C2=NNC=C2)C1C1=CN(C2CCNCC2)N=C1C1=CC=NC=C1 RCBZCSONTXNSHW-UHFFFAOYSA-N 0.000 claims 1
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims 1
- RICPRHNLFHUQIT-UHFFFAOYSA-N 5-(1-methyl-3-pyridin-4-ylpyrazol-4-yl)-1,3-dihydroindol-2-one Chemical compound N=1N(C)C=C(C=2C=C3CC(=O)NC3=CC=2)C=1C1=CC=NC=C1 RICPRHNLFHUQIT-UHFFFAOYSA-N 0.000 claims 1
- NWAIAPGJHCMCJQ-UHFFFAOYSA-N 5-(1-methyl-3-pyridin-4-ylpyrazol-4-yl)-2,3-dihydroinden-1-one Chemical compound N=1N(C)C=C(C=2C=C3CCC(=O)C3=CC=2)C=1C1=CC=NC=C1 NWAIAPGJHCMCJQ-UHFFFAOYSA-N 0.000 claims 1
- XIWGEASMKDCYFJ-UHFFFAOYSA-N 5-(5-pyridin-4-yl-1h-pyrazol-4-yl)-2,3-dihydroinden-1-one Chemical compound C=1C=C2C(=O)CCC2=CC=1C1=CNN=C1C1=CC=NC=C1 XIWGEASMKDCYFJ-UHFFFAOYSA-N 0.000 claims 1
- CACKWIAQZGWUDK-UHFFFAOYSA-N 5-[1-(1-methylpiperidin-4-yl)-3-pyridin-4-ylpyrazol-4-yl]-3h-isoindol-1-amine Chemical compound C1CN(C)CCC1N1N=C(C=2C=CN=CC=2)C(C=2C=C3CNC(=N)C3=CC=2)=C1 CACKWIAQZGWUDK-UHFFFAOYSA-N 0.000 claims 1
- DEZZLWQELQORIU-UHFFFAOYSA-N 5-[1-(2-hydroxyethyl)-3-pyridin-4-yl-4-pyrazolyl]-2,3-dihydroinden-1-one oxime Chemical compound N=1N(CCO)C=C(C=2C=C3CCC(C3=CC=2)=NO)C=1C1=CC=NC=C1 DEZZLWQELQORIU-UHFFFAOYSA-N 0.000 claims 1
- MGGQMXLSPADSGN-UHFFFAOYSA-N 5-[1-(2-hydroxyethyl)-3-pyridin-4-ylpyrazol-4-yl]-1,3-dihydroindol-2-one Chemical compound N=1N(CCO)C=C(C=2C=C3CC(=O)NC3=CC=2)C=1C1=CC=NC=C1 MGGQMXLSPADSGN-UHFFFAOYSA-N 0.000 claims 1
- UMUDEJRSKACPSS-UHFFFAOYSA-N 5-[1-(2-hydroxyethyl)-3-pyridin-4-ylpyrazol-4-yl]-1h-quinazolin-4-one Chemical compound N=1N(CCO)C=C(C=2C=3C(=O)NC=NC=3C=CC=2)C=1C1=CC=NC=C1 UMUDEJRSKACPSS-UHFFFAOYSA-N 0.000 claims 1
- XRDGWIKOQYEFOL-UHFFFAOYSA-N 5-[1-(2-hydroxyethyl)-3-pyridin-4-ylpyrazol-4-yl]-2,3-dihydroinden-1-one Chemical compound N=1N(CCO)C=C(C=2C=C3CCC(=O)C3=CC=2)C=1C1=CC=NC=C1 XRDGWIKOQYEFOL-UHFFFAOYSA-N 0.000 claims 1
- UIBKJNFSKLXWTK-UHFFFAOYSA-N 5-[1-(2-hydroxyethyl)-3-pyridin-4-ylpyrazol-4-yl]-2,3-dihydrophthalazine-1,4-dione Chemical compound N=1N(CCO)C=C(C=2C3=C(C(NNC3=O)=O)C=CC=2)C=1C1=CC=NC=C1 UIBKJNFSKLXWTK-UHFFFAOYSA-N 0.000 claims 1
- VFWDUSGVXPKDHF-UHFFFAOYSA-N 5-[1-(2-hydroxyethyl)-3-pyridin-4-ylpyrazol-4-yl]-2-(2-methoxyethyl)isoindole-1,3-dione Chemical compound C1=C2C(=O)N(CCOC)C(=O)C2=CC=C1C1=CN(CCO)N=C1C1=CC=NC=C1 VFWDUSGVXPKDHF-UHFFFAOYSA-N 0.000 claims 1
- YNEHWTFXTODKTQ-UHFFFAOYSA-N 5-[1-(2-hydroxyethyl)-3-pyridin-4-ylpyrazol-4-yl]-2h-isoquinolin-1-one Chemical compound N=1N(CCO)C=C(C=2C3=CC=NC(O)=C3C=CC=2)C=1C1=CC=NC=C1 YNEHWTFXTODKTQ-UHFFFAOYSA-N 0.000 claims 1
- SZOSXNZCMNUXFR-UHFFFAOYSA-N 5-[1-[2-(4-methylpiperazin-1-yl)ethyl]-3-pyridin-4-ylpyrazol-4-yl]-2,3-dihydro-1h-inden-1-amine Chemical compound C1CN(C)CCN1CCN1N=C(C=2C=CN=CC=2)C(C=2C=C3CCC(N)C3=CC=2)=C1 SZOSXNZCMNUXFR-UHFFFAOYSA-N 0.000 claims 1
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims 1
- HXGBUKKPDSRQTR-UHFFFAOYSA-N 6-(1-methyl-3-pyridin-4-ylpyrazol-4-yl)naphthalen-1-ol Chemical compound N=1N(C)C=C(C=2C=C3C=CC=C(O)C3=CC=2)C=1C1=CC=NC=C1 HXGBUKKPDSRQTR-UHFFFAOYSA-N 0.000 claims 1
- RILYHIWSBNWFIQ-GMAHTHKFSA-N 6-[1-[(1s,2s)-2-hydroxycyclohexyl]-3-pyridin-4-ylpyrazol-4-yl]naphthalen-1-ol Chemical compound O[C@H]1CCCC[C@@H]1N1N=C(C=2C=CN=CC=2)C(C=2C=C3C=CC=C(O)C3=CC=2)=C1 RILYHIWSBNWFIQ-GMAHTHKFSA-N 0.000 claims 1
- 208000010507 Adenocarcinoma of Lung Diseases 0.000 claims 1
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- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 1
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- RMTGMEXYMKRUSY-UHFFFAOYSA-N N-[5-(1-methyl-5-pyridin-4-ylpyrazol-4-yl)-2,3-dihydroinden-1-ylidene]hydroxylamine Chemical compound CN1N=CC(C=2C=C3CCC(C3=CC=2)=NO)=C1C1=CC=NC=C1 RMTGMEXYMKRUSY-UHFFFAOYSA-N 0.000 claims 1
- HNYYFWGWLSEHQF-UHFFFAOYSA-N N-[5-(5-pyridin-4-yl-1H-pyrazol-4-yl)-2,3-dihydroinden-1-ylidene]hydroxylamine Chemical compound C=1C=C2C(=NO)CCC2=CC=1C1=CNN=C1C1=CC=NC=C1 HNYYFWGWLSEHQF-UHFFFAOYSA-N 0.000 claims 1
- BFXCZPXEDHBYBJ-UHFFFAOYSA-N N-[5-[1-(1-methylpiperidin-4-yl)-3-pyridin-4-ylpyrazol-4-yl]-3H-isoindol-1-yl]hydroxylamine Chemical compound C1CN(C)CCC1N1N=C(C=2C=CN=CC=2)C(C=2C=C3CNC(/C3=CC=2)=N\O)=C1 BFXCZPXEDHBYBJ-UHFFFAOYSA-N 0.000 claims 1
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- 2006-02-02 BR BRPI0607346-8A patent/BRPI0607346A2/pt not_active IP Right Cessation
- 2006-02-02 US US11/345,828 patent/US7491829B2/en not_active Expired - Fee Related
- 2006-02-02 RU RU2007133111/04A patent/RU2007133111A/ru not_active Application Discontinuation
- 2006-02-02 CA CA002596973A patent/CA2596973A1/en not_active Abandoned
- 2006-02-02 JP JP2007554205A patent/JP2008530011A/ja active Pending
- 2006-02-02 EP EP06734199A patent/EP1846391A2/en not_active Withdrawn
- 2006-02-02 AU AU2006210626A patent/AU2006210626A1/en not_active Abandoned
- 2006-02-02 KR KR1020077020119A patent/KR20070107104A/ko not_active Withdrawn
- 2006-02-02 WO PCT/US2006/003654 patent/WO2006084015A2/en not_active Ceased
- 2006-02-02 CN CNA2006800109351A patent/CN101282960A/zh active Pending
- 2006-02-02 MX MX2007009405A patent/MX2007009405A/es not_active Application Discontinuation
- 2006-02-03 AR ARP060100401A patent/AR053014A1/es not_active Application Discontinuation
-
2007
- 2007-08-02 IL IL185024A patent/IL185024A0/en unknown
- 2007-08-17 MA MA30151A patent/MA29310B1/fr unknown
- 2007-08-28 ZA ZA200707289A patent/ZA200707289B/xx unknown
- 2007-09-03 NO NO20074473A patent/NO20074473L/no not_active Application Discontinuation
- 2007-09-04 CR CR9365A patent/CR9365A/es not_active Application Discontinuation
-
2008
- 2008-12-31 US US12/347,412 patent/US20090176809A1/en not_active Abandoned
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