JP2010529145A5 - - Google Patents
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- JP2010529145A5 JP2010529145A5 JP2010511393A JP2010511393A JP2010529145A5 JP 2010529145 A5 JP2010529145 A5 JP 2010529145A5 JP 2010511393 A JP2010511393 A JP 2010511393A JP 2010511393 A JP2010511393 A JP 2010511393A JP 2010529145 A5 JP2010529145 A5 JP 2010529145A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- aryl
- composition
- optionally substituted
- fluoro
- 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 description 125
- 125000003118 aryl group Chemical group 0.000 claims description 92
- 125000000217 alkyl group Chemical group 0.000 claims description 70
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 55
- 241001465754 Metazoa Species 0.000 claims description 46
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims description 43
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims description 41
- 229910052757 nitrogen Inorganic materials 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 36
- 125000000623 heterocyclic group Chemical group 0.000 claims description 32
- 125000001153 fluoro group Chemical group F* 0.000 claims description 28
- 125000001072 heteroaryl group Chemical group 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 28
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 27
- 230000015654 memory Effects 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- -1 -NR a R b Chemical group 0.000 claims description 18
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 239000001301 oxygen Substances 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000004043 oxo group Chemical group O=* 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 208000010877 cognitive disease Diseases 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- 208000024827 Alzheimer disease Diseases 0.000 claims description 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 6
- 230000003920 cognitive function Effects 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 230000007787 long-term memory Effects 0.000 claims description 5
- 208000020016 psychiatric disease Diseases 0.000 claims description 5
- 230000006403 short-term memory Effects 0.000 claims description 5
- 241000124008 Mammalia Species 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
- 230000004770 neurodegeneration Effects 0.000 claims description 3
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 230000001105 regulatory effect Effects 0.000 claims description 3
- 208000019901 Anxiety disease Diseases 0.000 claims description 2
- 201000000980 schizophrenia Diseases 0.000 claims description 2
- 208000019116 sleep disease Diseases 0.000 claims description 2
- 208000020685 sleep-wake disease Diseases 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 239000003937 drug carrier Substances 0.000 claims 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 56
- 238000000034 method Methods 0.000 description 56
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 38
- 238000005160 1H NMR spectroscopy Methods 0.000 description 32
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 238000012549 training Methods 0.000 description 19
- 102000005962 receptors Human genes 0.000 description 13
- 108020003175 receptors Proteins 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 12
- 210000000287 oocyte Anatomy 0.000 description 11
- 150000003254 radicals Chemical class 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 239000003814 drug Substances 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 9
- 125000004122 cyclic group Chemical group 0.000 description 9
- 230000008569 process Effects 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- 210000004556 brain Anatomy 0.000 description 7
- 239000002299 complementary DNA Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 230000014759 maintenance of location Effects 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000033228 biological regulation Effects 0.000 description 6
- 239000012320 chlorinating reagent Substances 0.000 description 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
- 230000004044 response Effects 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 238000003556 assay Methods 0.000 description 5
- 229940049706 benzodiazepine Drugs 0.000 description 5
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000013612 plasmid Substances 0.000 description 5
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 4
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 4
- REUOCJLVDZPJEK-UHFFFAOYSA-N 3-chlorocinnoline Chemical compound C1=CC=C2N=NC(Cl)=CC2=C1 REUOCJLVDZPJEK-UHFFFAOYSA-N 0.000 description 4
- VMPCBEQFWHYVIV-UHFFFAOYSA-N C1=CC=N[C]2N[C]3C=NN=C3C=C21 Chemical class C1=CC=N[C]2N[C]3C=NN=C3C=C21 VMPCBEQFWHYVIV-UHFFFAOYSA-N 0.000 description 4
- 241000283984 Rodentia Species 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 230000027455 binding Effects 0.000 description 4
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 230000006870 function Effects 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 3
- CXUGAWWYKSOLEL-UHFFFAOYSA-N 2h-cinnolin-3-one Chemical compound C1=CC=C2N=NC(O)=CC2=C1 CXUGAWWYKSOLEL-UHFFFAOYSA-N 0.000 description 3
- HHRYDDRWORXLOW-UHFFFAOYSA-N C1CN(C)CCN1C1=CC=C(NC=C2C(N(C=3N=CC=CC=3)N=C22)=O)C2=N1 Chemical compound C1CN(C)CCN1C1=CC=C(NC=C2C(N(C=3N=CC=CC=3)N=C22)=O)C2=N1 HHRYDDRWORXLOW-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000282412 Homo Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- UVZAIPRVSOBFOL-UHFFFAOYSA-N O=C1N(C=2C=CC=CC=2)N=C(C2=CC=N3)C1=CNC2=C3N1CCNCC1 Chemical compound O=C1N(C=2C=CC=CC=2)N=C(C2=CC=N3)C1=CNC2=C3N1CCNCC1 UVZAIPRVSOBFOL-UHFFFAOYSA-N 0.000 description 3
- PWUABIOOZPIRRX-UHFFFAOYSA-N O=C1N(C=2C=CC=CC=2)N=C(C2=CN=3)C1=CNC2=CC=3N1CCNCC1 Chemical compound O=C1N(C=2C=CC=CC=2)N=C(C2=CN=3)C1=CNC2=CC=3N1CCNCC1 PWUABIOOZPIRRX-UHFFFAOYSA-N 0.000 description 3
- XZDABLUPZIKEAS-UHFFFAOYSA-N O=C1N(C=2C=CC=CC=2)N=C(C2=N3)C1=CNC2=CC=C3N1CCNCC1 Chemical compound O=C1N(C=2C=CC=CC=2)N=C(C2=N3)C1=CNC2=CC=C3N1CCNCC1 XZDABLUPZIKEAS-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 239000000556 agonist Substances 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 231100000673 dose–response relationship Toxicity 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 230000010412 perfusion Effects 0.000 description 3
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 3
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- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 2
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical compound C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 description 2
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- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 1
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- 238000001953 recrystallisation Methods 0.000 description 1
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- 230000002787 reinforcement Effects 0.000 description 1
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- 125000006413 ring segment Chemical group 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
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- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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| PCT/US2008/066211 WO2008154447A1 (en) | 2007-06-08 | 2008-06-06 | Therapeutic pyrazolonaphthyridine derivatives |
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| EP (1) | EP2166853B1 (enExample) |
| JP (1) | JP2010529145A (enExample) |
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| US7863266B2 (en) * | 2007-06-08 | 2011-01-04 | Helicon Therapeutics, Inc. | Therapeutic pyrazoloquinoline urea derivatives |
| US9012470B2 (en) | 2010-10-14 | 2015-04-21 | Dart Neuroscience (Cayman) Ltd. | Therapeutic 5,6,5-tricyclic analogs |
| US20150374705A1 (en) | 2012-02-14 | 2015-12-31 | Shanghai Institues for Biological Sciences | Substances for treatment or relief of pain |
| US10531200B2 (en) * | 2015-10-23 | 2020-01-07 | Harman International Industries, Incorporated | Dual asymmetric compression driver |
| CN106810550A (zh) * | 2017-01-10 | 2017-06-09 | 湖南华腾制药有限公司 | 一种萘啶衍生物的制备方法 |
| US11485733B2 (en) | 2017-06-30 | 2022-11-01 | Bayer Animal Health Gmbh | Azaquinoline derivatives |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3204126A1 (de) * | 1982-02-06 | 1983-08-11 | Bayer Ag, 5090 Leverkusen | Pyrazoloxazine, -thiazine, -chinoline, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| US4479955A (en) * | 1983-01-10 | 1984-10-30 | Ciba-Geigy Corporation | Heterocycle-fused pyrazolo[3,4-d]pyridin-3-ones as benzodiazepine receptor modulators |
| US4814450A (en) | 1984-07-09 | 1989-03-21 | Ciba-Geigy Corporation | Certain ring-fused pyrazolo[3,4-d]-pyridin-3-one derivatives |
| JPS61112075A (ja) * | 1984-11-05 | 1986-05-30 | Shionogi & Co Ltd | チエニルピラゾロキノリン誘導体 |
| EP0214092A1 (en) | 1985-08-08 | 1987-03-11 | Ciba-Geigy Ag | Enhanced absorption of psychoactive 2-aryl-pyrazolo quinolines as a solid molecular dispersion in polyvinylpyrrolidone |
| US4817450A (en) * | 1987-11-30 | 1989-04-04 | Spedco, Inc. | Pressure/temperature test plug assembly |
| FR2695126B1 (fr) * | 1992-08-27 | 1994-11-10 | Sanofi Elf | Dérivés d'acide thiényl ou pyrrolyl carboxyliques, leur préparation et médicaments les contenant. |
| US5334595A (en) * | 1992-10-23 | 1994-08-02 | Sterling Winthrop Inc. | Pyrazoloquinolones as anticancer agents |
| RU2145606C1 (ru) * | 1994-05-24 | 2000-02-20 | Ф.Хоффманн-Ля Рош Аг | Трициклические дикарбонильные производные и лекарственный препарат на их основе |
| GB9716344D0 (en) * | 1997-08-01 | 1997-10-08 | Merck Sharp & Dohme | Therapeutic compounds |
| GB9716347D0 (en) * | 1997-08-01 | 1997-10-08 | Merck Sharp & Dohme | Therapeutic compounds |
| GB9716345D0 (en) * | 1997-08-01 | 1997-10-08 | Merck Sharp & Dohme | Therapeutic compounds |
| TWI271406B (en) * | 1999-12-13 | 2007-01-21 | Eisai Co Ltd | Tricyclic condensed heterocyclic compounds, preparation method of the same and pharmaceuticals comprising the same |
| GB0108475D0 (en) * | 2001-04-04 | 2001-05-23 | Merck Sharp & Dohme | New compounds |
| JP3896309B2 (ja) * | 2001-07-09 | 2007-03-22 | ファイザー株式会社 | プロテインキナーゼｃ阻害物質としてのピラゾロキノリノン誘導体 |
| ATE425164T1 (de) * | 2002-12-16 | 2009-03-15 | Active Biotech Ab | Tetrazyklische immunmodulierende verbindungen |
| AR045689A1 (es) * | 2003-05-29 | 2005-11-09 | Millennium Pharm Inc | Compuestos derivados de 2,5-dihidro-pirazolo[4,3-c]quinolin-4-ona como inhibidores de chk-1 y composiciones farmaceuticas que los contienen |
| US7544697B2 (en) * | 2003-10-03 | 2009-06-09 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and analogs thereof |
| CN1893943A (zh) * | 2003-10-03 | 2007-01-10 | 3M创新有限公司 | 吡唑并吡啶和其类似物 |
| AU2006287378A1 (en) * | 2005-09-07 | 2007-03-15 | Braincells, Inc. | Modulation of neurogenesis by HDac inhibition |
| ES2386168T3 (es) * | 2007-06-08 | 2012-08-10 | Helicon Therapeutics, Inc. | Derivados de pirazoloquinolina terapéuticos |
-
2008
- 2008-06-06 ES ES08770412.8T patent/ES2483728T3/es active Active
- 2008-06-06 US US12/135,045 patent/US7858614B2/en not_active Expired - Fee Related
- 2008-06-06 JP JP2010511393A patent/JP2010529145A/ja active Pending
- 2008-06-06 CA CA2689934A patent/CA2689934A1/en not_active Abandoned
- 2008-06-06 MX MX2009013197A patent/MX2009013197A/es active IP Right Grant
- 2008-06-06 BR BRPI0812369A patent/BRPI0812369A2/pt not_active IP Right Cessation
- 2008-06-06 KR KR1020107000331A patent/KR20100036306A/ko not_active Withdrawn
- 2008-06-06 AU AU2008261803A patent/AU2008261803A1/en not_active Abandoned
- 2008-06-06 CN CN200880025152A patent/CN101754681A/zh active Pending
- 2008-06-06 EP EP08770412.8A patent/EP2166853B1/en not_active Not-in-force
- 2008-06-06 WO PCT/US2008/066211 patent/WO2008154447A1/en not_active Ceased
-
2009
- 2009-11-23 IL IL202287A patent/IL202287A0/en unknown
-
2010
- 2010-11-18 US US12/949,619 patent/US8497262B2/en not_active Expired - Fee Related
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