JP2011520896A5 - - Google Patents
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- JP2011520896A5 JP2011520896A5 JP2011509628A JP2011509628A JP2011520896A5 JP 2011520896 A5 JP2011520896 A5 JP 2011520896A5 JP 2011509628 A JP2011509628 A JP 2011509628A JP 2011509628 A JP2011509628 A JP 2011509628A JP 2011520896 A5 JP2011520896 A5 JP 2011520896A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- hydrogen
- pharmaceutically acceptable
- acceptable salt
- compound
- 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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- 229910052739 hydrogen Inorganic materials 0.000 claims description 91
- 239000001257 hydrogen Substances 0.000 claims description 91
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 53
- 125000006239 protecting group Chemical group 0.000 claims description 6
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 claims description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 4
- 229940126657 Compound 17 Drugs 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 2
- 235000019270 ammonium chloride Nutrition 0.000 claims description 2
- 230000005595 deprotonation Effects 0.000 claims description 2
- 238000010537 deprotonation reaction Methods 0.000 claims description 2
- 238000006138 lithiation reaction Methods 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 68
- 150000001875 compounds Chemical class 0.000 claims 60
- 150000003839 salts Chemical class 0.000 claims 55
- -1 3-chloro-4-fluorophenyl Chemical group 0.000 claims 50
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 44
- 125000004429 atom Chemical group 0.000 claims 36
- 150000002431 hydrogen Chemical class 0.000 claims 35
- 229910052736 halogen Inorganic materials 0.000 claims 26
- 150000002367 halogens Chemical class 0.000 claims 26
- 239000000203 mixture Substances 0.000 claims 24
- 125000003118 aryl group Chemical group 0.000 claims 23
- 125000001072 heteroaryl group Chemical group 0.000 claims 22
- 125000000623 heterocyclic group Chemical group 0.000 claims 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims 20
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 17
- 229920006395 saturated elastomer Polymers 0.000 claims 15
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 14
- 239000012623 DNA damaging agent Substances 0.000 claims 14
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 11
- 206010028980 Neoplasm Diseases 0.000 claims 9
- 201000011510 cancer Diseases 0.000 claims 9
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 9
- 125000004043 oxo group Chemical group O=* 0.000 claims 8
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 claims 7
- GAGWJHPBXLXJQN-UORFTKCHSA-N Capecitabine Chemical compound C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1[C@H]1[C@H](O)[C@H](O)[C@@H](C)O1 GAGWJHPBXLXJQN-UORFTKCHSA-N 0.000 claims 7
- GAGWJHPBXLXJQN-UHFFFAOYSA-N Capecitabine Natural products C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1C1C(O)C(O)C(C)O1 GAGWJHPBXLXJQN-UHFFFAOYSA-N 0.000 claims 7
- UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 claims 7
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims 7
- BPEGJWRSRHCHSN-UHFFFAOYSA-N Temozolomide Chemical compound O=C1N(C)N=NC2=C(C(N)=O)N=CN21 BPEGJWRSRHCHSN-UHFFFAOYSA-N 0.000 claims 7
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 7
- 229940127093 camptothecin Drugs 0.000 claims 7
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 claims 7
- 229960004117 capecitabine Drugs 0.000 claims 7
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims 7
- 229960004316 cisplatin Drugs 0.000 claims 7
- 229960000684 cytarabine Drugs 0.000 claims 7
- 201000010099 disease Diseases 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 claims 7
- 229960002949 fluorouracil Drugs 0.000 claims 7
- 229960005277 gemcitabine Drugs 0.000 claims 7
- SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 claims 7
- UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 claims 7
- 229960004768 irinotecan Drugs 0.000 claims 7
- 229960004964 temozolomide Drugs 0.000 claims 7
- 230000003463 hyperproliferative effect Effects 0.000 claims 6
- 238000004519 manufacturing process Methods 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 5
- 238000010276 construction Methods 0.000 claims 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[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
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 2
- 206010009944 Colon cancer Diseases 0.000 claims 2
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 2
- 101000777293 Homo sapiens Serine/threonine-protein kinase Chk1 Proteins 0.000 claims 2
- 206010033128 Ovarian cancer Diseases 0.000 claims 2
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 2
- 102100031081 Serine/threonine-protein kinase Chk1 Human genes 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 239000003112 inhibitor Substances 0.000 claims 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 2
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims 2
- 201000002528 pancreatic cancer Diseases 0.000 claims 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 2
- 125000004262 quinoxalin-2-yl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N=C1* 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 1
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001847 2-phenylcyclopropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1([H])C([H])([H])C1([H])* 0.000 claims 1
- WJRKNLONLOMALV-UHFFFAOYSA-N 5-chloropyridine Chemical compound ClC1=C=NC=C[CH]1 WJRKNLONLOMALV-UHFFFAOYSA-N 0.000 claims 1
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 230000001093 anti-cancer Effects 0.000 claims 1
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 238000003419 tautomerization reaction Methods 0.000 claims 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
- 241000349731 Afzelia bipindensis Species 0.000 description 1
- ZYOUZMYPAWIGKT-UHFFFAOYSA-N CCCC(C)C(C)N=C Chemical compound CCCC(C)C(C)N=C ZYOUZMYPAWIGKT-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229940126142 compound 16 Drugs 0.000 description 1
- 239000012039 electrophile Substances 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5292608P | 2008-05-13 | 2008-05-13 | |
| US61/052,926 | 2008-05-13 | ||
| PCT/US2009/043691 WO2009140320A1 (en) | 2008-05-13 | 2009-05-13 | Pyrrolopyridines as kinase inhibitors |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015032474A Division JP2015098482A (ja) | 2008-05-13 | 2015-02-23 | キナーゼ阻害剤としてのピロロピリジン |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011520896A JP2011520896A (ja) | 2011-07-21 |
| JP2011520896A5 true JP2011520896A5 (enExample) | 2014-07-31 |
| JP5703212B2 JP5703212B2 (ja) | 2015-04-15 |
Family
ID=40810786
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011509628A Expired - Fee Related JP5703212B2 (ja) | 2008-05-13 | 2009-05-13 | キナーゼ阻害剤としてのピロロピリジン |
| JP2015032474A Withdrawn JP2015098482A (ja) | 2008-05-13 | 2015-02-23 | キナーゼ阻害剤としてのピロロピリジン |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015032474A Withdrawn JP2015098482A (ja) | 2008-05-13 | 2015-02-23 | キナーゼ阻害剤としてのピロロピリジン |
Country Status (30)
| Country | Link |
|---|---|
| US (6) | US8178131B2 (enExample) |
| EP (2) | EP2990407B1 (enExample) |
| JP (2) | JP5703212B2 (enExample) |
| KR (2) | KR101657856B1 (enExample) |
| CN (3) | CN104926810B (enExample) |
| AR (1) | AR071717A1 (enExample) |
| AU (1) | AU2009246402B2 (enExample) |
| BR (1) | BRPI0913580B8 (enExample) |
| CA (1) | CA2724262C (enExample) |
| CL (1) | CL2009001152A1 (enExample) |
| CO (1) | CO6321244A2 (enExample) |
| CR (1) | CR11803A (enExample) |
| CY (1) | CY1116692T1 (enExample) |
| DK (1) | DK2307409T3 (enExample) |
| ES (1) | ES2552643T3 (enExample) |
| HK (1) | HK1219950A1 (enExample) |
| HR (1) | HRP20151018T1 (enExample) |
| HU (1) | HUE026160T2 (enExample) |
| IL (1) | IL209258A (enExample) |
| MX (1) | MX2010012449A (enExample) |
| NZ (1) | NZ589318A (enExample) |
| PH (1) | PH12013501779B1 (enExample) |
| PL (1) | PL2307409T3 (enExample) |
| PT (1) | PT2307409E (enExample) |
| RS (1) | RS54358B1 (enExample) |
| RU (1) | RU2517194C2 (enExample) |
| SI (1) | SI2307409T1 (enExample) |
| TW (2) | TWI554512B (enExample) |
| UA (1) | UA111933C2 (enExample) |
| WO (1) | WO2009140320A1 (enExample) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101959887B (zh) | 2008-01-08 | 2013-07-31 | 阵列生物制药公司 | 作为激酶抑制剂的吡咯并吡啶 |
| ES2392014T3 (es) | 2008-01-09 | 2012-12-03 | Array Biopharma, Inc. | Pirazolopiridinas como inhibidores de la cinasa |
| JP2009256298A (ja) * | 2008-03-26 | 2009-11-05 | Sumitomo Chemical Co Ltd | ピペリジン−３−イルカーバメート化合物の光学分割方法およびその中間体 |
| AR071717A1 (es) * | 2008-05-13 | 2010-07-07 | Array Biopharma Inc | Pirrolo[2,3-b]piridinas inhibidoras de quinasas chk1 y chk2,composiciones farmaceuticas que las contienen,proceso para prepararlas y uso de las mismas en el tratamiento y prevencion del cancer. |
| US8481557B2 (en) | 2009-04-11 | 2013-07-09 | Array Biopharma Inc. | Method of treatment using checkpoint kinase 1 inhibitors |
| BRPI1013920A2 (pt) * | 2009-04-11 | 2016-04-05 | Array Biopharma Inc | inibidores de ponto de checagem de quinase 1 para potencializar agentes de danificação de dna |
| TWI466885B (zh) | 2009-07-31 | 2015-01-01 | Japan Tobacco Inc | 含氮螺環化合物及其醫藥用途 |
| US9029359B2 (en) * | 2009-09-04 | 2015-05-12 | Biogen Idec Ma, Inc. | Heteroaryl Btk inhibitors |
| RU2563644C2 (ru) | 2010-08-20 | 2015-09-20 | Хатчисон Медифарма Лимитед | Пирролопиримидиновые соединения и их применения |
| RU2627841C2 (ru) | 2010-11-16 | 2017-08-14 | Эррэй Биофарма Инк. | Комбинация ингибиторов чекпойнт-киназы 1 и ингибиторов киназы wee 1 |
| RU2598846C2 (ru) | 2011-02-25 | 2016-09-27 | Эррэй Биофарма Инк. | Триазолопиридиновые соединения как ингибиторы киназы pim |
| CA2834166A1 (en) | 2011-04-29 | 2012-11-01 | Amgen Inc. | Bicyclic pyridazine compounds as pim inhibitors |
| GB201201566D0 (en) | 2012-01-30 | 2012-03-14 | Vernalis R&D Ltd | New chemical compounds |
| CA2871436C (en) | 2012-04-23 | 2020-07-28 | Genentech, Inc. | Intermediates and processes for preparing compounds for use as chk1 inhibitors |
| US9993460B2 (en) | 2013-07-26 | 2018-06-12 | Race Oncology Ltd. | Compositions to improve the therapeutic benefit of bisantrene and analogs and derivatives thereof |
| EP3036227B1 (en) * | 2013-08-22 | 2020-01-08 | Genentech, Inc. | Process for preparing a compound |
| WO2015027090A1 (en) * | 2013-08-22 | 2015-02-26 | Genentech, Inc. | Intermediates and processes for preparing compounds |
| RU2018142605A (ru) * | 2013-09-25 | 2019-02-04 | Вертекс Фармасьютикалз Инкорпорейтед | Селективный ингибитор фосфатидилинозитол-3-киназы-гамма |
| JP6783224B2 (ja) | 2014-04-04 | 2020-11-11 | デル マー ファーマシューティカルズ | 肺の非小細胞癌腫及び卵巣癌を処置するためのジアンヒドロガラクチトール及びその類縁体又は誘導体の使用 |
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