JP2011510055A5 - - Google Patents
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- Publication number
- JP2011510055A5 JP2011510055A5 JP2010543556A JP2010543556A JP2011510055A5 JP 2011510055 A5 JP2011510055 A5 JP 2011510055A5 JP 2010543556 A JP2010543556 A JP 2010543556A JP 2010543556 A JP2010543556 A JP 2010543556A JP 2011510055 A5 JP2011510055 A5 JP 2011510055A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- phenyl
- methyl
- fluoro
- pyrazole
- 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.)
- Granted
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- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 23
- 150000001875 compounds Chemical class 0.000 claims 20
- 239000001257 hydrogen Substances 0.000 claims 15
- 229910052739 hydrogen Inorganic materials 0.000 claims 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 11
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 11
- 229910052757 nitrogen Inorganic materials 0.000 claims 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 10
- 150000002431 hydrogen Chemical class 0.000 claims 9
- -1 hydroxy, methyl Chemical group 0.000 claims 8
- 239000000203 mixture Substances 0.000 claims 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 102000001253 Protein Kinase Human genes 0.000 claims 5
- 125000001153 fluoro group Chemical group F* 0.000 claims 5
- 108060006633 protein kinase Proteins 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- 230000000694 effects Effects 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 239000001301 oxygen Substances 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 239000011593 sulfur Chemical group 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 241000124008 Mammalia Species 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- 230000005764 inhibitory process Effects 0.000 claims 3
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 101000777293 Homo sapiens Serine/threonine-protein kinase Chk1 Proteins 0.000 claims 2
- 102100031081 Serine/threonine-protein kinase Chk1 Human genes 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 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 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 208000024891 symptom Diseases 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- GEBXRQMORXJPGN-UHFFFAOYSA-N 1-[(4-methylphenyl)methyl]-n-[6-oxo-5-[5-(piperidin-1-ylmethyl)-1h-indol-2-yl]-1h-pyridin-3-yl]pyrazole-4-carboxamide Chemical compound C1=CC(C)=CC=C1CN1N=CC(C(=O)NC=2C=C(C(=O)NC=2)C=2NC3=CC=C(CN4CCCCC4)C=C3C=2)=C1 GEBXRQMORXJPGN-UHFFFAOYSA-N 0.000 claims 1
- YRNZHBVRTDDGNB-UHFFFAOYSA-N 1-benzyl-n-[5-(1h-indol-2-yl)-6-oxo-1h-pyridin-3-yl]pyrazole-4-carboxamide Chemical compound C=1NC(=O)C(C=2NC3=CC=CC=C3C=2)=CC=1NC(=O)C(=C1)C=NN1CC1=CC=CC=C1 YRNZHBVRTDDGNB-UHFFFAOYSA-N 0.000 claims 1
- DISCGKGWZKLOSH-UHFFFAOYSA-N 1-benzyl-n-[5-[5-(2,2-dimethyl-3-piperidin-1-ylpropoxy)-1h-indol-2-yl]-6-oxo-1h-pyridin-3-yl]pyrazole-4-carboxamide Chemical compound C1CCCCN1CC(C)(C)COC(C=C1C=2)=CC=C1NC=2C(C(NC=1)=O)=CC=1NC(=O)C(=C1)C=NN1CC1=CC=CC=C1 DISCGKGWZKLOSH-UHFFFAOYSA-N 0.000 claims 1
- ZSYVTFSMHIZBJT-UHFFFAOYSA-N 1-benzyl-n-[5-[5-(2,2-dimethyl-3-pyrrolidin-1-ylpropoxy)-1h-indol-2-yl]-6-oxo-1h-pyridin-3-yl]pyrazole-4-carboxamide Chemical compound C1CCCN1CC(C)(C)COC(C=C1C=2)=CC=C1NC=2C(C(NC=1)=O)=CC=1NC(=O)C(=C1)C=NN1CC1=CC=CC=C1 ZSYVTFSMHIZBJT-UHFFFAOYSA-N 0.000 claims 1
- DKDWHPAIWPQMDV-UHFFFAOYSA-N 1-benzyl-n-[5-[5-[(4-fluoropiperidin-1-yl)methyl]-1h-indol-2-yl]-6-oxo-1h-pyridin-3-yl]pyrazole-4-carboxamide Chemical compound C1CC(F)CCN1CC1=CC=C(NC(=C2)C=3C(NC=C(NC(=O)C4=CN(CC=5C=CC=CC=5)N=C4)C=3)=O)C2=C1 DKDWHPAIWPQMDV-UHFFFAOYSA-N 0.000 claims 1
- QENZBLJVRSQXHR-UHFFFAOYSA-N 1-benzyl-n-[5-[5-[(4-methylpiperidin-1-yl)methyl]-1h-indol-2-yl]-6-oxo-1h-pyridin-3-yl]pyrazole-4-carboxamide Chemical compound C1CC(C)CCN1CC1=CC=C(NC(=C2)C=3C(NC=C(NC(=O)C4=CN(CC=5C=CC=CC=5)N=C4)C=3)=O)C2=C1 QENZBLJVRSQXHR-UHFFFAOYSA-N 0.000 claims 1
- OUZSVHBSAIWGAB-UHFFFAOYSA-N 1-benzyl-n-[5-[5-[1-(dimethylamino)-2-methylpropan-2-yl]oxy-1h-indol-2-yl]-6-oxo-1h-pyridin-3-yl]pyrazole-4-carboxamide Chemical compound C=1C2=CC(OC(C)(C)CN(C)C)=CC=C2NC=1C(C(NC=1)=O)=CC=1NC(=O)C(=C1)C=NN1CC1=CC=CC=C1 OUZSVHBSAIWGAB-UHFFFAOYSA-N 0.000 claims 1
- WMBKHLMCZPQUSY-UHFFFAOYSA-N 1-benzyl-n-[5-[5-[3-(diethylamino)-2,2-dimethylpropoxy]-1h-indol-2-yl]-6-oxo-1h-pyridin-3-yl]pyrazole-4-carboxamide Chemical compound C=1C2=CC(OCC(C)(C)CN(CC)CC)=CC=C2NC=1C(C(NC=1)=O)=CC=1NC(=O)C(=C1)C=NN1CC1=CC=CC=C1 WMBKHLMCZPQUSY-UHFFFAOYSA-N 0.000 claims 1
- REQMZUHAMVOEON-UHFFFAOYSA-N 1-benzyl-n-[5-[5-[3-(dimethylamino)-2,2-dimethylpropoxy]-1h-indol-2-yl]-6-oxo-1h-pyridin-3-yl]pyrazole-4-carboxamide Chemical compound C=1C2=CC(OCC(C)(C)CN(C)C)=CC=C2NC=1C(C(NC=1)=O)=CC=1NC(=O)C(=C1)C=NN1CC1=CC=CC=C1 REQMZUHAMVOEON-UHFFFAOYSA-N 0.000 claims 1
- PZNCUDMYMQBNPI-OAQYLSRUSA-N 1-benzyl-n-[5-[5-[[(2r)-2-methylpiperidin-1-yl]methyl]-1h-indol-2-yl]-6-oxo-1h-pyridin-3-yl]pyrazole-4-carboxamide Chemical compound C[C@@H]1CCCCN1CC1=CC=C(NC(=C2)C=3C(NC=C(NC(=O)C4=CN(CC=5C=CC=CC=5)N=C4)C=3)=O)C2=C1 PZNCUDMYMQBNPI-OAQYLSRUSA-N 0.000 claims 1
- ITWISLBDFHAZFK-OYRHEFFESA-N 1-benzyl-n-[5-[5-[[(2r,6s)-2,6-dimethylmorpholin-4-yl]methyl]-1h-indol-2-yl]-6-oxo-1h-pyridin-3-yl]pyrazole-4-carboxamide Chemical compound C1[C@@H](C)O[C@@H](C)CN1CC1=CC=C(NC(=C2)C=3C(NC=C(NC(=O)C4=CN(CC=5C=CC=CC=5)N=C4)C=3)=O)C2=C1 ITWISLBDFHAZFK-OYRHEFFESA-N 0.000 claims 1
- KIBWTTYZBWVWLR-SZPZYZBQSA-N 1-benzyl-n-[5-[5-[[(2r,6s)-2,6-dimethylpiperidin-1-yl]methyl]-1h-indol-2-yl]-6-oxo-1h-pyridin-3-yl]pyrazole-4-carboxamide Chemical compound C[C@H]1CCC[C@@H](C)N1CC1=CC=C(NC(=C2)C=3C(NC=C(NC(=O)C4=CN(CC=5C=CC=CC=5)N=C4)C=3)=O)C2=C1 KIBWTTYZBWVWLR-SZPZYZBQSA-N 0.000 claims 1
- PZNCUDMYMQBNPI-NRFANRHFSA-N 1-benzyl-n-[5-[5-[[(2s)-2-methylpiperidin-1-yl]methyl]-1h-indol-2-yl]-6-oxo-1h-pyridin-3-yl]pyrazole-4-carboxamide Chemical compound C[C@H]1CCCCN1CC1=CC=C(NC(=C2)C=3C(NC=C(NC(=O)C4=CN(CC=5C=CC=CC=5)N=C4)C=3)=O)C2=C1 PZNCUDMYMQBNPI-NRFANRHFSA-N 0.000 claims 1
- NOMVGDXJBPVSOA-UHFFFAOYSA-N 1-benzyl-n-[5-[5-[[[3-(dimethylamino)-2,2-dimethylpropyl]-ethylamino]methyl]-1h-indol-2-yl]-6-oxo-1h-pyridin-3-yl]pyrazole-4-carboxamide Chemical compound C=1C2=CC(CN(CC)CC(C)(C)CN(C)C)=CC=C2NC=1C(C(NC=1)=O)=CC=1NC(=O)C(=C1)C=NN1CC1=CC=CC=C1 NOMVGDXJBPVSOA-UHFFFAOYSA-N 0.000 claims 1
- OEKPFDMUKNSTBS-UHFFFAOYSA-N 1-benzyl-n-[6-oxo-5-[5-(piperidin-1-ylmethyl)-1h-indol-2-yl]-1h-pyridin-3-yl]pyrazole-4-carboxamide Chemical compound C1=NN(CC=2C=CC=CC=2)C=C1C(=O)NC(C=1)=CNC(=O)C=1C(NC1=CC=2)=CC1=CC=2CN1CCCCC1 OEKPFDMUKNSTBS-UHFFFAOYSA-N 0.000 claims 1
- KGDOHXYALMXHLF-UHFFFAOYSA-N 1-benzylpyrazole-4-carboxylic acid Chemical compound C1=C(C(=O)O)C=NN1CC1=CC=CC=C1 KGDOHXYALMXHLF-UHFFFAOYSA-N 0.000 claims 1
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 206010052779 Transplant rejections Diseases 0.000 claims 1
- 230000005856 abnormality Effects 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 230000001363 autoimmune Effects 0.000 claims 1
- 238000002512 chemotherapy Methods 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000000824 cytostatic agent Substances 0.000 claims 1
- 239000002254 cytotoxic agent Substances 0.000 claims 1
- 229940127089 cytotoxic agent Drugs 0.000 claims 1
- 231100000599 cytotoxic agent Toxicity 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 206010025135 lupus erythematosus Diseases 0.000 claims 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- APAITVFDOPBSBV-UHFFFAOYSA-N n-[5-[5-[(4-fluoropiperidin-1-yl)methyl]-1h-indol-2-yl]-6-oxo-1h-pyridin-3-yl]-1-(1-phenylethyl)pyrazole-4-carboxamide Chemical compound C1=C(C(=O)NC=2C=C(C(=O)NC=2)C=2NC3=CC=C(CN4CCC(F)CC4)C=C3C=2)C=NN1C(C)C1=CC=CC=C1 APAITVFDOPBSBV-UHFFFAOYSA-N 0.000 claims 1
- WZFHXTBJQNYCNB-BHIFYINESA-N n-[5-[5-[[(2r,6s)-2,6-dimethylmorpholin-4-yl]methyl]-1h-indol-2-yl]-6-oxo-1h-pyridin-3-yl]-1-[(1r)-1-phenylethyl]pyrazole-4-carboxamide Chemical compound C1([C@@H](C)N2N=CC(=C2)C(=O)NC=2C=C(C(=O)NC=2)C=2NC3=CC=C(CN4C[C@@H](C)O[C@@H](C)C4)C=C3C=2)=CC=CC=C1 WZFHXTBJQNYCNB-BHIFYINESA-N 0.000 claims 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
- 210000000056 organ Anatomy 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 238000001959 radiotherapy Methods 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0801090.2 | 2008-01-22 | ||
| GBGB0801090.2A GB0801090D0 (en) | 2008-01-22 | 2008-01-22 | New chemical compounds |
| GBGB0818695.9A GB0818695D0 (en) | 2008-10-11 | 2008-10-11 | New chemical compounds |
| GB0818695.9 | 2008-10-11 | ||
| PCT/GB2009/000149 WO2009093012A1 (en) | 2008-01-22 | 2009-01-20 | Indolyl- pyridone derivatives having checkpoint kinase 1 inhibitory activity |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011510055A JP2011510055A (ja) | 2011-03-31 |
| JP2011510055A5 true JP2011510055A5 (https=) | 2012-03-01 |
| JP5386508B2 JP5386508B2 (ja) | 2014-01-15 |
Family
ID=40377594
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010543556A Expired - Fee Related JP5386508B2 (ja) | 2008-01-22 | 2009-01-20 | インドリル−ピリドン誘導体類 |
Country Status (17)
| Country | Link |
|---|---|
| US (5) | US8916591B2 (https=) |
| EP (1) | EP2294065B1 (https=) |
| JP (1) | JP5386508B2 (https=) |
| CN (1) | CN101970424B (https=) |
| AU (1) | AU2009207478B2 (https=) |
| BR (1) | BRPI0906495B8 (https=) |
| CA (1) | CA2712959C (https=) |
| DK (1) | DK2294065T3 (https=) |
| EA (1) | EA021464B1 (https=) |
| ES (1) | ES2461799T3 (https=) |
| IL (1) | IL206808A (https=) |
| MX (1) | MX2010007525A (https=) |
| NZ (1) | NZ586756A (https=) |
| PL (1) | PL2294065T3 (https=) |
| PT (1) | PT2294065E (https=) |
| WO (1) | WO2009093012A1 (https=) |
| ZA (1) | ZA201005210B (https=) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK2294065T3 (da) | 2008-01-22 | 2014-04-28 | Vernalis R&D Ltd | Indolyl-pyridonderivater med checkpoint kinase 1 inhibitorisk aktivitet |
| GB0912499D0 (en) * | 2009-07-18 | 2009-08-26 | Vernalis R&D Ltd | Indopyl-pyridone derivatives |
| JP6161537B2 (ja) | 2010-04-07 | 2017-07-12 | エフ・ホフマン−ラ・ロシュ・アクチェンゲゼルシャフト | ピラゾール−４−イル−ヘテロシクリル−カルボキサミド化合物及び使用の方法 |
| EP2463289A1 (en) * | 2010-11-26 | 2012-06-13 | Almirall, S.A. | Imidazo[1,2-b]pyridazine derivatives as JAK inhibitors |
| EP2760857A1 (en) | 2011-09-27 | 2014-08-06 | F.Hoffmann-La Roche Ag | Pyrazol-4-yl-heterocyclyl-carboxamide compounds and methods of use |
| GB201201566D0 (en) * | 2012-01-30 | 2012-03-14 | Vernalis R&D Ltd | New chemical compounds |
| CN112472699A (zh) | 2013-07-26 | 2021-03-12 | 种族肿瘤学公司 | 改善比生群及衍生物的治疗益处的组合方法 |
| TN2017000329A1 (en) * | 2015-01-28 | 2019-01-16 | Bayer Pharma AG | 4h-pyrrolo[3,2-c]pyridin-4-one derivatives |
| JP7313354B2 (ja) * | 2017-12-19 | 2023-07-24 | ブリストル－マイヤーズ スクイブ カンパニー | Ｔｌｒ阻害剤として有用なアミド置換されたインドール化合物 |
| MA53377A (fr) * | 2018-07-24 | 2021-06-02 | Epizyme Inc | Composés de pyridin-2-one utiles en tant qu'antagonistes de smarca2 |
| US10280721B1 (en) | 2018-07-27 | 2019-05-07 | Upwing Energy, LLC | Artificial lift |
| US10253606B1 (en) | 2018-07-27 | 2019-04-09 | Upwing Energy, LLC | Artificial lift |
| US10370947B1 (en) * | 2018-07-27 | 2019-08-06 | Upwing Energy, LLC | Artificial lift |
| US10787873B2 (en) | 2018-07-27 | 2020-09-29 | Upwing Energy, LLC | Recirculation isolator for artificial lift and method of use |
| ES2985569T3 (es) * | 2018-08-24 | 2024-11-06 | Transthera Sciences Nanjing Inc | Nuevo inhibidor de derivado de quinolina |
| US11686161B2 (en) | 2018-12-28 | 2023-06-27 | Upwing Energy, Inc. | System and method of transferring power within a wellbore |
| CN112625027B (zh) * | 2019-09-24 | 2022-09-09 | 药捷安康(南京)科技股份有限公司 | 杂环衍生物及其用途 |
| US20230414624A1 (en) * | 2022-06-24 | 2023-12-28 | Enalare Therapeutics Inc. | Methods of treating neurological ventilatory insufficiency |
| CN115594634B (zh) * | 2022-10-26 | 2024-10-01 | 浙江工业大学 | 一种连续化制备4-硝基吡唑的新工艺 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GEP20053660B (en) * | 2001-03-28 | 2005-11-10 | Bristol Myers Squibb Co | Novel Tyrosine Kinase Inhibitors |
| BR0213562A (pt) | 2001-10-26 | 2004-08-31 | Aventis Pharma Inc | Benzimidazóis e análogos e seu uso como inibidores de cinases de proteìna |
| US20050256157A1 (en) * | 2002-08-23 | 2005-11-17 | Chiron Corporation | Combination therapy with CHK1 inhibitors |
| JP2006526654A (ja) | 2003-06-05 | 2006-11-24 | メルク エンド カムパニー インコーポレーテッド | 置換インドールおよび置換インドールの調製方法 |
| TWI372050B (en) * | 2003-07-03 | 2012-09-11 | Astex Therapeutics Ltd | (morpholin-4-ylmethyl-1h-benzimidazol-2-yl)-1h-pyrazoles |
| CA2600914A1 (en) * | 2005-01-28 | 2007-07-26 | Mark E. Fraley | Inhibitors of checkpoint kinases |
| JP2008545776A (ja) | 2005-06-11 | 2008-12-18 | ヴァーナリス アールアンドディー リミテッド | 癌および自己免疫疾患の治療における使用のためのピラゾール−置換ベンズイミダゾール誘導体 |
| EP2046330A2 (en) * | 2006-07-14 | 2009-04-15 | Astex Therapeutics Limited | Pharmaceutical combinations |
| WO2008025526A1 (en) * | 2006-08-31 | 2008-03-06 | F. Hoffmann-La Roche Ag | Indole derivatives, their manufacture and use as pharmaceutical agents |
| DK2294065T3 (da) | 2008-01-22 | 2014-04-28 | Vernalis R&D Ltd | Indolyl-pyridonderivater med checkpoint kinase 1 inhibitorisk aktivitet |
| MX2011012202A (es) * | 2009-05-15 | 2011-12-08 | Novartis Ag | Derivados de 5-piridin-3-il-1,3-dihidro-indol-2-ona y su uso como moduladores de a sintanasa de aldosterona y/o de cyp11b1. |
-
2009
- 2009-01-20 DK DK09704645T patent/DK2294065T3/da active
- 2009-01-20 CN CN200980103188XA patent/CN101970424B/zh not_active Expired - Fee Related
- 2009-01-20 JP JP2010543556A patent/JP5386508B2/ja not_active Expired - Fee Related
- 2009-01-20 PL PL09704645T patent/PL2294065T3/pl unknown
- 2009-01-20 CA CA2712959A patent/CA2712959C/en not_active Expired - Fee Related
- 2009-01-20 EA EA201001197A patent/EA021464B1/ru not_active IP Right Cessation
- 2009-01-20 US US12/812,791 patent/US8916591B2/en not_active Expired - Fee Related
- 2009-01-20 AU AU2009207478A patent/AU2009207478B2/en not_active Ceased
- 2009-01-20 NZ NZ586756A patent/NZ586756A/en not_active IP Right Cessation
- 2009-01-20 EP EP20090704645 patent/EP2294065B1/en not_active Not-in-force
- 2009-01-20 MX MX2010007525A patent/MX2010007525A/es active IP Right Grant
- 2009-01-20 BR BRPI0906495A patent/BRPI0906495B8/pt not_active IP Right Cessation
- 2009-01-20 PT PT09704645T patent/PT2294065E/pt unknown
- 2009-01-20 WO PCT/GB2009/000149 patent/WO2009093012A1/en not_active Ceased
- 2009-01-20 ES ES09704645T patent/ES2461799T3/es active Active
-
2010
- 2010-07-05 IL IL206808A patent/IL206808A/en active IP Right Grant
- 2010-07-21 ZA ZA2010/05210A patent/ZA201005210B/en unknown
-
2014
- 2014-11-10 US US14/536,764 patent/US9604975B2/en not_active Expired - Fee Related
-
2017
- 2017-02-08 US US15/427,457 patent/US20170298043A1/en not_active Abandoned
-
2018
- 2018-04-25 US US15/962,306 patent/US10696652B2/en not_active Expired - Fee Related
-
2020
- 2020-05-28 US US16/886,276 patent/US20200361905A1/en not_active Abandoned
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