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 (cg-RX-API-DMAC7.html) | 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)
Families Citing this family (36)
| 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 |
| US8372842B2 (en) | 2008-01-09 | 2013-02-12 | Array Biopharma Inc. | Pyrazolopyridines as kinase inhibitors |
| 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 |
| CL2009001152A1 (es) | 2008-05-13 | 2009-10-16 | Array Biopharma Inc | Compuestos derivados de n-(4-(cicloalquilo nitrogenado-1-il)-1h-pirrolo[2,3-b]piridin-3-il)amida, inhibidores de cinasa; proceso de preparacion; composicion farmaceutica; y su uso para el tratamiento de una enfermedad proliferativa. |
| 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 |
| US8481557B2 (en) * | 2009-04-11 | 2013-07-09 | Array Biopharma Inc. | Method of treatment using checkpoint kinase 1 inhibitors |
| TWI466885B (zh) | 2009-07-31 | 2015-01-01 | Japan Tobacco Inc | 含氮螺環化合物及其醫藥用途 |
| EP2485589A4 (en) * | 2009-09-04 | 2013-02-06 | Biogen Idec Inc | HETEROARYL-BTK INHIBITORS |
| CN103119045B (zh) | 2010-08-20 | 2016-02-17 | 和记黄埔医药（上海）有限公司 | 吡咯并嘧啶化合物及其用途 |
| TW201304778A (zh) | 2010-11-16 | 2013-02-01 | Array Biopharma Inc | 檢查點激酶１抑制劑及ｗｅｅ１激酶抑制劑之組合 |
| UA111075C2 (uk) | 2011-02-25 | 2016-03-25 | Еррей Біофарма Інк. | Триазолопіридинові сполуки як інгібітори кінази рім |
| WO2012148775A1 (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 |
| KR102096679B1 (ko) | 2012-04-23 | 2020-04-02 | 제넨테크, 인크. | 화합물의 제조를 위한 중간체 및 방법 |
| CA2938626A1 (en) | 2013-07-26 | 2015-01-29 | John Rothman | Compositions to improve the therapeutic benefit of bisantrene |
| WO2015027090A1 (en) * | 2013-08-22 | 2015-02-26 | Genentech, Inc. | Intermediates and processes for preparing compounds |
| JP6463758B2 (ja) * | 2013-08-22 | 2019-02-06 | ジェネンテック， インコーポレイテッド | 化合物の調製方法 |
| CN105722838B (zh) * | 2013-09-25 | 2017-10-24 | 沃泰克斯药物股份有限公司 | 磷脂酰肌醇3‑激酶‑γ的选择性抑制剂 |
| KR102359214B1 (ko) | 2014-04-04 | 2022-02-07 | 델 마 파마슈티컬스 | 폐의 비소세포 암종 및 난소암을 치료하기 위한 디안하이드로갈락티톨 및 이의 유사체 또는 유도체 |
| US9580416B2 (en) | 2014-07-02 | 2017-02-28 | Pharmacyclics Llc | Inhibitors of Bruton's tyrosine kinase |
| MA41599A (fr) * | 2015-02-26 | 2018-01-02 | Array Biopharma Inc | Formes cristallines d'un composé pyrrolopyridine |
| WO2017003090A1 (ko) | 2015-06-30 | 2017-01-05 | 서울바이오시스 주식회사 | Uv led가 적용된 포충기 |
| KR20250133463A (ko) | 2015-11-04 | 2025-09-05 | 메르크 파텐트 게엠베하 | Btk 억제 활성을 갖는 피리미딘 및 피리딘 화합물을 사용하여 암 치료하는 방법 |
| JP2018538330A (ja) * | 2015-12-22 | 2018-12-27 | ヴァイティー ファーマシューティカルズ，インコーポレイテッド | ｍｅｎｉｎ−ＭＬＬ相互作用の阻害剤 |
| PL3468966T3 (pl) | 2016-06-10 | 2021-04-06 | Vitae Pharmaceuticals, Llc | Inhibitory interakcji menina-mll |
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