JP2015536306A5 - - Google Patents
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- Publication number
- JP2015536306A5 JP2015536306A5 JP2015536951A JP2015536951A JP2015536306A5 JP 2015536306 A5 JP2015536306 A5 JP 2015536306A5 JP 2015536951 A JP2015536951 A JP 2015536951A JP 2015536951 A JP2015536951 A JP 2015536951A JP 2015536306 A5 JP2015536306 A5 JP 2015536306A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- methyl
- phenyl
- carbonyl
- benzenesulfonamide
- 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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- -1 C 1-6 alkyl-OH Chemical group 0.000 claims description 67
- 150000001875 compounds Chemical class 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- 230000035772 mutation Effects 0.000 claims description 20
- 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 description 20
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 15
- 206010028980 Neoplasm Diseases 0.000 claims description 13
- 201000011510 cancer Diseases 0.000 claims description 13
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 101000599886 Homo sapiens Isocitrate dehydrogenase [NADP], mitochondrial Proteins 0.000 claims description 10
- 102100037845 Isocitrate dehydrogenase [NADP], mitochondrial Human genes 0.000 claims description 10
- 101001042041 Bos taurus Isocitrate dehydrogenase [NAD] subunit beta, mitochondrial Proteins 0.000 claims description 9
- 101000960234 Homo sapiens Isocitrate dehydrogenase [NADP] cytoplasmic Proteins 0.000 claims description 9
- 102100039905 Isocitrate dehydrogenase [NADP] cytoplasmic Human genes 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 201000003793 Myelodysplastic syndrome Diseases 0.000 claims description 8
- 201000007224 Myeloproliferative neoplasm Diseases 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- OEYGXEYESNDHQS-UHFFFAOYSA-N 1-(2-methyl-5-piperidin-1-ylsulfonylphenyl)-3-(3,5,7-trimethyl-1-adamantyl)urea Chemical compound C1=C(NC(=O)NC23CC4(C)CC(C)(CC(C4)(C)C2)C3)C(C)=CC=C1S(=O)(=O)N1CCCCC1 OEYGXEYESNDHQS-UHFFFAOYSA-N 0.000 claims description 6
- CYCFHZPFMAXQRB-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[5-morpholin-4-ylsulfonyl-2-(2-oxopyrrolidin-1-yl)phenyl]urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC1=CC(S(=O)(=O)N2CCOCC2)=CC=C1N1C(=O)CCC1 CYCFHZPFMAXQRB-UHFFFAOYSA-N 0.000 claims description 6
- JADAACJWFPKJSC-UHFFFAOYSA-N 1-[2-(diethylamino)-5-morpholin-4-ylsulfonylphenyl]-3-(3-methylphenyl)urea Chemical compound CCN(CC)C1=CC=C(S(=O)(=O)N2CCOCC2)C=C1NC(=O)NC1=CC=CC(C)=C1 JADAACJWFPKJSC-UHFFFAOYSA-N 0.000 claims description 6
- RSIFRBLCVZDPFI-UHFFFAOYSA-N 1-[3-(azepan-1-ylsulfonyl)-4-methylphenyl]-3-[2-(3-prop-1-en-2-ylphenyl)propan-2-yl]urea Chemical compound CC(=C)C1=CC=CC(C(C)(C)NC(=O)NC=2C=C(C(C)=CC=2)S(=O)(=O)N2CCCCCC2)=C1 RSIFRBLCVZDPFI-UHFFFAOYSA-N 0.000 claims description 6
- GUNQZZMJRXGITI-UHFFFAOYSA-N 1-[3-[(2-methoxyphenyl)sulfamoyl]-4-piperidin-1-ylphenyl]-3-[2-(3-prop-1-en-2-ylphenyl)propan-2-yl]urea Chemical compound COC1=CC=CC=C1NS(=O)(=O)C1=CC(NC(=O)NC(C)(C)C=2C=C(C=CC=2)C(C)=C)=CC=C1N1CCCCC1 GUNQZZMJRXGITI-UHFFFAOYSA-N 0.000 claims description 6
- AQEFBMVFUWQQGA-UHFFFAOYSA-N 1-[3-[(3-chlorophenyl)sulfamoyl]-4-methylphenyl]-3-[2-(3-prop-1-en-2-ylphenyl)propan-2-yl]urea Chemical compound CC(=C)C1=CC=CC(C(C)(C)NC(=O)NC=2C=C(C(C)=CC=2)S(=O)(=O)NC=2C=C(Cl)C=CC=2)=C1 AQEFBMVFUWQQGA-UHFFFAOYSA-N 0.000 claims description 6
- JMMZFYORIQSJKO-UHFFFAOYSA-N 1-[4-(diethylamino)-3-[(2-methoxyphenyl)sulfamoyl]phenyl]-3-[2-(3-prop-1-en-2-ylphenyl)propan-2-yl]urea Chemical compound C1=C(S(=O)(=O)NC=2C(=CC=CC=2)OC)C(N(CC)CC)=CC=C1NC(=O)NC(C)(C)C1=CC=CC(C(C)=C)=C1 JMMZFYORIQSJKO-UHFFFAOYSA-N 0.000 claims description 6
- XOFACLCJHFUIDE-UHFFFAOYSA-N 1-[4-chloro-3-[(4-ethoxyphenyl)sulfamoyl]phenyl]-3-[2-(3-prop-1-en-2-ylphenyl)propan-2-yl]urea Chemical compound C1=CC(OCC)=CC=C1NS(=O)(=O)C1=CC(NC(=O)NC(C)(C)C=2C=C(C=CC=2)C(C)=C)=CC=C1Cl XOFACLCJHFUIDE-UHFFFAOYSA-N 0.000 claims description 6
- VAZOYARPRLVOKK-UHFFFAOYSA-N 1-[5-(butylsulfamoyl)-2-methoxyphenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CCCCNS(=O)(=O)C1=CC=C(OC)C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 VAZOYARPRLVOKK-UHFFFAOYSA-N 0.000 claims description 6
- HRKRDXGIYSURLR-UHFFFAOYSA-N 1-[5-[(2,5-dichlorophenyl)sulfamoyl]-2-(diethylamino)phenyl]-3-(4-nitrophenyl)urea Chemical compound CCN(CC)C1=CC=C(S(=O)(=O)NC=2C(=CC=C(Cl)C=2)Cl)C=C1NC(=O)NC1=CC=C([N+]([O-])=O)C=C1 HRKRDXGIYSURLR-UHFFFAOYSA-N 0.000 claims description 6
- JDUBSDSPWVKMFO-UHFFFAOYSA-N 1-[5-[3-[2,4-bis(2-methylbutan-2-yl)phenoxy]propylsulfamoyl]-2-chlorophenyl]-3-(3,5-dichloro-2-hydroxy-4-methylphenyl)urea Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=CC=C1OCCCNS(=O)(=O)C1=CC=C(Cl)C(NC(=O)NC=2C(=C(Cl)C(C)=C(Cl)C=2)O)=C1 JDUBSDSPWVKMFO-UHFFFAOYSA-N 0.000 claims description 6
- DVNJUHFYDMTVCU-UHFFFAOYSA-N 1-[5-[[4-[bis(2-hydroxyethyl)amino]-2-methylphenyl]methylidene]-2-phenylimidazol-4-yl]-3-[5-(hexadecylsulfamoyl)-2-methoxyphenyl]urea Chemical compound CCCCCCCCCCCCCCCCNS(=O)(=O)C1=CC=C(OC)C(NC(=O)NC=2C(N=C(N=2)C=2C=CC=CC=2)=CC=2C(=CC(=CC=2)N(CCO)CCO)C)=C1 DVNJUHFYDMTVCU-UHFFFAOYSA-N 0.000 claims description 6
- GSPWDUPQFBOLPX-UHFFFAOYSA-N 1-[6-[4-[bis(2-cyanoethyl)amino]-2-methylphenyl]imino-3,4-dicyano-5-(trifluoromethyl)pyrrolo[1,2-b]pyrazol-2-yl]-3-[2-chloro-5-(hexadecylsulfamoyl)phenyl]urea Chemical compound CCCCCCCCCCCCCCCCNS(=O)(=O)c1ccc(Cl)c(NC(=O)Nc2nn3C(=Nc4ccc(cc4C)N(CCC#N)CCC#N)C(=C(C#N)c3c2C#N)C(F)(F)F)c1 GSPWDUPQFBOLPX-UHFFFAOYSA-N 0.000 claims description 6
- KRYZQVQMDSSVHM-UHFFFAOYSA-N 3-(4-chloro-3-pyrrolidin-1-ylsulfonylphenyl)-1-methyl-1-[(2-methyl-1,3-thiazol-5-yl)methyl]urea Chemical compound C=1C=C(Cl)C(S(=O)(=O)N2CCCC2)=CC=1NC(=O)N(C)CC1=CN=C(C)S1 KRYZQVQMDSSVHM-UHFFFAOYSA-N 0.000 claims description 6
- YLOIWATYZNZGIC-UHFFFAOYSA-N 3-(4-methoxy-3-piperidin-1-ylsulfonylphenyl)-1-methyl-1-[(2-methyl-1,3-thiazol-5-yl)methyl]urea Chemical compound C1=C(S(=O)(=O)N2CCCCC2)C(OC)=CC=C1NC(=O)N(C)CC1=CN=C(C)S1 YLOIWATYZNZGIC-UHFFFAOYSA-N 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- LDZOUHCRTQBWTF-UHFFFAOYSA-O n-[4-[[5-[3-(4-butyl-3,5-dimethylpyridin-1-ium-1-yl)propylcarbamoylamino]-2-chlorophenyl]sulfonylamino]anilino]formamide Chemical compound C1=C(C)C(CCCC)=C(C)C=[N+]1CCCNC(=O)NC1=CC=C(Cl)C(S(=O)(=O)NC=2C=CC(NNC=O)=CC=2)=C1 LDZOUHCRTQBWTF-UHFFFAOYSA-O 0.000 claims description 6
- IJAIFRUQXADQJV-UHFFFAOYSA-N n-[4-[[5-[3-(4-butyl-3,5-dimethylpyridin-1-ium-1-yl)propylcarbamoylamino]-2-chlorophenyl]sulfonylamino]anilino]formamide;chloride Chemical compound [Cl-].C1=C(C)C(CCCC)=C(C)C=[N+]1CCCNC(=O)NC1=CC=C(Cl)C(S(=O)(=O)NC=2C=CC(NNC=O)=CC=2)=C1 IJAIFRUQXADQJV-UHFFFAOYSA-N 0.000 claims description 6
- RIHISJPMISXXNE-UHFFFAOYSA-N n-[5-chloro-3-[[4-chloro-3-(dodecylsulfamoyl)phenyl]carbamoylamino]-2-hydroxyphenyl]acetamide Chemical compound C1=C(Cl)C(S(=O)(=O)NCCCCCCCCCCCC)=CC(NC(=O)NC=2C(=C(NC(C)=O)C=C(Cl)C=2)O)=C1 RIHISJPMISXXNE-UHFFFAOYSA-N 0.000 claims description 6
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 6
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 6
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 4
- HWXBTNAVRSUOJR-UHFFFAOYSA-N 2-hydroxyglutaric acid Chemical compound OC(=O)C(O)CCC(O)=O HWXBTNAVRSUOJR-UHFFFAOYSA-N 0.000 claims description 4
- CTJVLIALFREFQS-UHFFFAOYSA-N 3-(4-ethoxy-3-pyrrolidin-1-ylsulfonylphenyl)-1-methyl-1-(4-methylcyclohexyl)urea Chemical compound C1=C(S(=O)(=O)N2CCCC2)C(OCC)=CC=C1NC(=O)N(C)C1CCC(C)CC1 CTJVLIALFREFQS-UHFFFAOYSA-N 0.000 claims description 4
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
- 208000005243 Chondrosarcoma Diseases 0.000 claims description 4
- 108090000790 Enzymes Proteins 0.000 claims description 4
- 102000004190 Enzymes Human genes 0.000 claims description 4
- 208000032612 Glial tumor Diseases 0.000 claims description 4
- 206010018338 Glioma Diseases 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 208000006990 cholangiocarcinoma Diseases 0.000 claims description 4
- 230000001419 dependent effect Effects 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 208000005017 glioblastoma Diseases 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 201000001441 melanoma Diseases 0.000 claims description 4
- 102200116484 rs121913502 Human genes 0.000 claims description 4
- 229940124597 therapeutic agent Drugs 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 2
- 206010004593 Bile duct cancer Diseases 0.000 claims description 2
- 206010009944 Colon cancer Diseases 0.000 claims description 2
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 2
- 206010039491 Sarcoma Diseases 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000003725 azepanyl group Chemical group 0.000 claims description 2
- 208000026900 bile duct neoplasm Diseases 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 2
- 102200069708 rs121913499 Human genes 0.000 claims description 2
- 102200069690 rs121913500 Human genes 0.000 claims description 2
- 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 description 2
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 2
- 125000004001 thioalkyl group Chemical group 0.000 claims description 2
- 230000002792 vascular Effects 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 3
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
- 238000000034 method Methods 0.000 description 12
- KNPYUBYMGCLBEJ-UHFFFAOYSA-N 1-[5-(azepan-1-ylsulfonyl)-2-chlorophenyl]-3-(4-nitrophenyl)urea Chemical compound C1=CC([N+](=O)[O-])=CC=C1NC(=O)NC1=CC(S(=O)(=O)N2CCCCCC2)=CC=C1Cl KNPYUBYMGCLBEJ-UHFFFAOYSA-N 0.000 description 3
- KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261714179P | 2012-10-15 | 2012-10-15 | |
| US61/714,179 | 2012-10-15 | ||
| PCT/US2013/064601 WO2014062511A1 (en) | 2012-10-15 | 2013-10-11 | Therapeutic compounds and compositions |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018130743A Division JP2018199677A (ja) | 2012-10-15 | 2018-07-10 | 治療化合物および組成物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015536306A JP2015536306A (ja) | 2015-12-21 |
| JP2015536306A5 true JP2015536306A5 (https=) | 2016-11-24 |
| JP6385352B2 JP6385352B2 (ja) | 2018-09-05 |
Family
ID=50488660
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015536951A Expired - Fee Related JP6385352B2 (ja) | 2012-10-15 | 2013-10-11 | 治療化合物および組成物 |
| JP2018130743A Withdrawn JP2018199677A (ja) | 2012-10-15 | 2018-07-10 | 治療化合物および組成物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018130743A Withdrawn JP2018199677A (ja) | 2012-10-15 | 2018-07-10 | 治療化合物および組成物 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US10202339B2 (https=) |
| EP (1) | EP2906212A4 (https=) |
| JP (2) | JP6385352B2 (https=) |
| CN (1) | CN104822373B (https=) |
| AU (1) | AU2013331626B2 (https=) |
| CA (1) | CA2888360A1 (https=) |
| HK (1) | HK1213798A1 (https=) |
| MX (1) | MX365747B (https=) |
| NZ (1) | NZ706999A (https=) |
| WO (1) | WO2014062511A1 (https=) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2561132C2 (ru) | 2009-06-29 | 2015-08-20 | Аджиос Фармасьютикалз, Инк. | Производные хинолинсульфонамидов и их применение для модулирования пкм2 активности |
| CN102827170A (zh) | 2011-06-17 | 2012-12-19 | 安吉奥斯医药品有限公司 | 治疗活性组合物和它们的使用方法 |
| US9474779B2 (en) | 2012-01-19 | 2016-10-25 | Agios Pharmaceuticals, Inc. | Therapeutically active compositions and their methods of use |
| CN105593215B (zh) | 2013-07-11 | 2019-01-15 | 安吉奥斯医药品有限公司 | 用于治疗癌症的作为idh2突变体抑制剂的2,4-或4,6-二氨基嘧啶化合物 |
| US9579324B2 (en) | 2013-07-11 | 2017-02-28 | Agios Pharmaceuticals, Inc | Therapeutically active compounds and their methods of use |
| WO2015003355A2 (en) | 2013-07-11 | 2015-01-15 | Agios Pharmaceuticals, Inc. | Therapeutically active compounds and their methods of use |
| WO2015003360A2 (en) | 2013-07-11 | 2015-01-15 | Agios Pharmaceuticals, Inc. | Therapeutically active compounds and their methods of use |
| US20150031627A1 (en) | 2013-07-25 | 2015-01-29 | Agios Pharmaceuticals, Inc | Therapeutically active compounds and their methods of use |
| KR20240010105A (ko) | 2014-03-14 | 2024-01-23 | 아지오스 파마슈티컬스 아이엔씨. | 치료적으로 활성인 화합물의 약제학적 조성물 |
| US20150273088A1 (en) * | 2014-03-28 | 2015-10-01 | Washington University | Zaprinast analogues as glutaminase inhibitors and methods to predict response thereto |
| EP3303286B1 (en) * | 2015-06-01 | 2023-10-04 | Cedars-Sinai Medical Center | Compounds that bind to rela of nf-kb for use in treating cancer |
| CN107922375B (zh) * | 2015-07-30 | 2020-05-22 | 正大天晴药业集团股份有限公司 | 靶向idh2突变的抗肿瘤化合物及其使用方法 |
| SG11201803088PA (en) | 2015-10-15 | 2018-05-30 | Agios Pharmaceuticals Inc | Combination therapy for treating malignancies |
| PT3362066T (pt) | 2015-10-15 | 2021-11-16 | Celgene Corp | Terapia de combinação para tratar malignidades |
| EP3412663B1 (en) * | 2016-02-04 | 2022-09-07 | Shionogi & Co., Ltd. | Nitrogen-containing heterocycle and carbocycle derivatives having trka inhibitory activity |
| WO2017140758A1 (en) | 2016-02-19 | 2017-08-24 | Debiopharm International S.A. | Derivatives of 2-amino-4-(2-oxazolidinon-3-yl)-pyrimidine fused with a five-membered heteroaromatic ring in 5,6-position which are useful for the treatment of various cancers |
| WO2017162156A1 (zh) * | 2016-03-22 | 2017-09-28 | 正大天晴药业集团股份有限公司 | 丙啶磺酰胺类化合物及其使用方法 |
| CN107556366B (zh) * | 2016-06-30 | 2025-02-07 | 上海海和药物研究开发股份有限公司 | 具有突变型异柠檬酸脱氢酶抑制活性的化合物、其制备方法及用途 |
| CN107973748A (zh) * | 2017-12-22 | 2018-05-01 | 潘劲松 | 含磺酸酯基或磺酰胺基的吡啶酮类偶氮分散染料及其合成方法 |
| PE20212329A1 (es) * | 2018-04-12 | 2021-12-14 | Eisai Randd Man Co Ltd | Derivados de pladeniolida como agentes dirigidos a empalmosoma para tratar el cancer |
| US10980788B2 (en) | 2018-06-08 | 2021-04-20 | Agios Pharmaceuticals, Inc. | Therapy for treating malignancies |
| IT201900001009A1 (it) | 2019-01-23 | 2020-07-23 | Torino Politecnico | Vettore nanoporoso biomimetico comprendente un inibitore diretto verso la forma nativa della proteina IDH2 |
| US12478614B2 (en) | 2020-01-21 | 2025-11-25 | Emory University | Inhibitors of glutathione s-transferases (GSTs) and NAD(P)H:quinone oxidoreductase 1 (NQO1), pharmaceutical compositions, and uses in managing cancer |
| CN112375069B (zh) * | 2020-11-20 | 2022-09-13 | 湖北民族大学 | 一种4-脲基嘧啶类化合物及其用途 |
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| BE754242A (fr) | 1970-07-15 | 1971-02-01 | Geigy Ag J R | Diamino-s-triazines et dinitro-s-triazines |
| US3867383A (en) | 1971-03-29 | 1975-02-18 | Ciba Geigy Corp | Monoanthranilatoanilino-s-triazines |
| CH606334A5 (https=) | 1974-06-21 | 1978-10-31 | Ciba Geigy Ag | |
| DE2928485A1 (de) * | 1979-07-14 | 1981-01-29 | Bayer Ag | Verwendung von harnstoffderivaten als arzneimittel bei der behandlung von fettstoffwechselstoerungen |
| JPS58186682A (ja) | 1982-04-27 | 1983-10-31 | 日本化薬株式会社 | セルロ−ス又はセルロ−ス含有繊維材料の染色法 |
| DE3512630A1 (de) | 1985-04-06 | 1986-10-23 | Hoechst Ag, 6230 Frankfurt | Verfahren zum faerben oder bedrucken von cellulosefasern oder cellulosemischfasern |
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-
2013
- 2013-10-11 WO PCT/US2013/064601 patent/WO2014062511A1/en not_active Ceased
- 2013-10-11 HK HK16101848.4A patent/HK1213798A1/zh unknown
- 2013-10-11 US US14/435,674 patent/US10202339B2/en not_active Expired - Fee Related
- 2013-10-11 CA CA2888360A patent/CA2888360A1/en active Pending
- 2013-10-11 JP JP2015536951A patent/JP6385352B2/ja not_active Expired - Fee Related
- 2013-10-11 NZ NZ706999A patent/NZ706999A/en not_active IP Right Cessation
- 2013-10-11 EP EP13846787.3A patent/EP2906212A4/en not_active Withdrawn
- 2013-10-11 CN CN201380062951.5A patent/CN104822373B/zh not_active Expired - Fee Related
- 2013-10-11 MX MX2015004762A patent/MX365747B/es active IP Right Grant
- 2013-10-11 AU AU2013331626A patent/AU2013331626B2/en not_active Ceased
-
2018
- 2018-07-10 JP JP2018130743A patent/JP2018199677A/ja not_active Withdrawn
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