JP2018516947A5 - - Google Patents
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- Publication number
- JP2018516947A5 JP2018516947A5 JP2017563544A JP2017563544A JP2018516947A5 JP 2018516947 A5 JP2018516947 A5 JP 2018516947A5 JP 2017563544 A JP2017563544 A JP 2017563544A JP 2017563544 A JP2017563544 A JP 2017563544A JP 2018516947 A5 JP2018516947 A5 JP 2018516947A5
- Authority
- JP
- Japan
- Prior art keywords
- dosage form
- oral dosage
- fluoro
- methyl
- cyclopenta
- 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.)
- Withdrawn
Links
- 239000006186 oral dosage form Substances 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 27
- QLLGKCJUPWYJON-HLTSFMKQSA-N roducitabine Chemical compound O=C1N=C(N)C=CN1[C@@H]1C(F)=C(CO)[C@@H](O)[C@H]1O QLLGKCJUPWYJON-HLTSFMKQSA-N 0.000 claims description 26
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 24
- 239000008346 aqueous phase Substances 0.000 claims description 20
- 102100037944 Integrator complex subunit 12 Human genes 0.000 claims description 19
- 101710149803 Integrator complex subunit 12 Proteins 0.000 claims description 19
- 239000012074 organic phase Substances 0.000 claims description 18
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 238000005406 washing Methods 0.000 claims description 16
- -1 [1,3] dioxol-4-yl Chemical group 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 14
- 239000000243 solution Substances 0.000 claims description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 10
- 238000010924 continuous production Methods 0.000 claims description 10
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 claims description 10
- 239000012141 concentrate Substances 0.000 claims description 8
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 claims description 8
- 239000012452 mother liquor Substances 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000002002 slurry Substances 0.000 claims description 8
- 239000012453 solvate Substances 0.000 claims description 8
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 claims description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 239000006286 aqueous extract Substances 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- VDCSGNNYCFPWFK-UHFFFAOYSA-N diphenylsilane Chemical compound C=1C=CC=CC=1[SiH2]C1=CC=CC=C1 VDCSGNNYCFPWFK-UHFFFAOYSA-N 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 101000841505 Homo sapiens Uridine-cytidine kinase 2 Proteins 0.000 claims description 5
- 102100029150 Uridine-cytidine kinase 2 Human genes 0.000 claims description 5
- FFOOUMJNSWFJQU-NLDZOOGBSA-N 1-[(3ar,6s,6as)-5-fluoro-2,2-dimethyl-4-(trityloxymethyl)-6,6a-dihydro-3ah-cyclopenta[d][1,3]dioxol-6-yl]-4-aminopyrimidin-2-one Chemical compound C=1([C@@H]2[C@H]([C@@H](C=1F)N1C(N=C(N)C=C1)=O)OC(O2)(C)C)COC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 FFOOUMJNSWFJQU-NLDZOOGBSA-N 0.000 claims description 4
- 102000008096 B7-H1 Antigen Human genes 0.000 claims description 4
- 108010074708 B7-H1 Antigen Proteins 0.000 claims description 4
- QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical compound CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 claims description 4
- 239000012359 Methanesulfonyl chloride Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 239000002246 antineoplastic agent Substances 0.000 claims description 4
- 238000003782 apoptosis assay Methods 0.000 claims description 4
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 4
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 4
- 210000004027 cell Anatomy 0.000 claims description 4
- 229940104302 cytosine Drugs 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 4
- 239000002574 poison Substances 0.000 claims description 4
- 231100000614 poison Toxicity 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 210000001519 tissue Anatomy 0.000 claims description 4
- LZTRCELOJRDYMQ-UHFFFAOYSA-N triphenylmethanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C1=CC=CC=C1 LZTRCELOJRDYMQ-UHFFFAOYSA-N 0.000 claims description 4
- 210000004881 tumor cell Anatomy 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 102100040678 Programmed cell death protein 1 Human genes 0.000 claims description 3
- 101710089372 Programmed cell death protein 1 Proteins 0.000 claims description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 3
- 229940034982 antineoplastic agent Drugs 0.000 claims description 3
- VNSQXWISTNFYFV-UHFFFAOYSA-N 1,3-dioxol-4-ol Chemical compound OC1=COCO1 VNSQXWISTNFYFV-UHFFFAOYSA-N 0.000 claims description 2
- CWFSKWMXGJLZBE-UHFFFAOYSA-N 6ah-cyclopenta[d][1,3]dioxol-6-ol Chemical compound O1COC2C(O)=CC=C21 CWFSKWMXGJLZBE-UHFFFAOYSA-N 0.000 claims description 2
- 206010005003 Bladder cancer Diseases 0.000 claims description 2
- 206010009944 Colon cancer Diseases 0.000 claims description 2
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 2
- 239000004971 Cross linker Substances 0.000 claims description 2
- 102000003915 DNA Topoisomerases Human genes 0.000 claims description 2
- 108090000323 DNA Topoisomerases Proteins 0.000 claims description 2
- 102000009058 Death Domain Receptors Human genes 0.000 claims description 2
- 108010049207 Death Domain Receptors Proteins 0.000 claims description 2
- 229940076838 Immune checkpoint inhibitor Drugs 0.000 claims description 2
- 102000037984 Inhibitory immune checkpoint proteins Human genes 0.000 claims description 2
- 108091008026 Inhibitory immune checkpoint proteins Proteins 0.000 claims description 2
- 102000016397 Methyltransferase Human genes 0.000 claims description 2
- 108060004795 Methyltransferase Proteins 0.000 claims description 2
- 102000029749 Microtubule Human genes 0.000 claims description 2
- 108091022875 Microtubule Proteins 0.000 claims description 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 2
- 229940123573 Protein synthesis inhibitor Drugs 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- 102000007537 Type II DNA Topoisomerases Human genes 0.000 claims description 2
- 108010046308 Type II DNA Topoisomerases Proteins 0.000 claims description 2
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N anhydrous trimethylamine Natural products CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 2
- 230000000340 anti-metabolite Effects 0.000 claims description 2
- 229940100197 antimetabolite Drugs 0.000 claims description 2
- 239000002256 antimetabolite Substances 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 238000013467 fragmentation Methods 0.000 claims description 2
- 238000006062 fragmentation reaction Methods 0.000 claims description 2
- 239000005556 hormone Substances 0.000 claims description 2
- 229940088597 hormone Drugs 0.000 claims description 2
- 239000003667 hormone antagonist Substances 0.000 claims description 2
- 239000012274 immune-checkpoint protein inhibitor Substances 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 238000003780 insertion Methods 0.000 claims description 2
- 230000037431 insertion Effects 0.000 claims description 2
- 239000000543 intermediate Substances 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 229940043355 kinase inhibitor Drugs 0.000 claims description 2
- 239000003446 ligand Substances 0.000 claims description 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 2
- 210000004688 microtubule Anatomy 0.000 claims description 2
- 201000002528 pancreatic cancer Diseases 0.000 claims description 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 2
- 239000003757 phosphotransferase inhibitor Substances 0.000 claims description 2
- 150000008442 polyphenolic compounds Chemical class 0.000 claims description 2
- 235000013824 polyphenols Nutrition 0.000 claims description 2
- 239000000007 protein synthesis inhibitor Substances 0.000 claims description 2
- 230000005855 radiation Effects 0.000 claims description 2
- 229940044601 receptor agonist Drugs 0.000 claims description 2
- 239000000018 receptor agonist Substances 0.000 claims description 2
- 102000005962 receptors Human genes 0.000 claims description 2
- 108020003175 receptors Proteins 0.000 claims description 2
- 230000001235 sensitizing effect Effects 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 208000024891 symptom Diseases 0.000 claims description 2
- 201000005112 urinary bladder cancer Diseases 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 6
- 241000282376 Panthera tigris Species 0.000 claims 1
- QWCSWYKXBPEIQM-KWXIBIRDSA-N [(3ar,6r,6ar)-5-fluoro-2,2-dimethyl-4-(trityloxymethyl)-6,6a-dihydro-3ah-cyclopenta[d][1,3]dioxol-6-yl] methanesulfonate Chemical compound FC([C@H](OS(C)(=O)=O)[C@@H]1OC(O[C@@H]11)(C)C)=C1COC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 QWCSWYKXBPEIQM-KWXIBIRDSA-N 0.000 claims 1
- 230000006907 apoptotic process Effects 0.000 claims 1
- 230000003796 beauty Effects 0.000 claims 1
- KBPHJBAIARWVSC-RGZFRNHPSA-N lutein Chemical compound C([C@H](O)CC=1C)C(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\[C@H]1C(C)=C[C@H](O)CC1(C)C KBPHJBAIARWVSC-RGZFRNHPSA-N 0.000 claims 1
- 229960005375 lutein Drugs 0.000 claims 1
- ORAKUVXRZWMARG-WZLJTJAWSA-N lutein Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C)C=CC=C(/C)C=CC2C(=CC(O)CC2(C)C)C ORAKUVXRZWMARG-WZLJTJAWSA-N 0.000 claims 1
- 235000012680 lutein Nutrition 0.000 claims 1
- 239000001656 lutein Substances 0.000 claims 1
- KBPHJBAIARWVSC-XQIHNALSSA-N trans-lutein Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C(=CC(O)CC2(C)C)C KBPHJBAIARWVSC-XQIHNALSSA-N 0.000 claims 1
- FJHBOVDFOQMZRV-XQIHNALSSA-N xanthophyll Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C=C(C)C(O)CC2(C)C FJHBOVDFOQMZRV-XQIHNALSSA-N 0.000 claims 1
- GXMPOSYLLAUPHN-UHFFFAOYSA-N CS(=O)(=O)OC1=COCO1 Chemical compound CS(=O)(=O)OC1=COCO1 GXMPOSYLLAUPHN-UHFFFAOYSA-N 0.000 description 1
- 0 NC(C=C*1([C@@]2C(F)=C(CO)[C@@]3O)[C@]23O)=NC1=O Chemical compound NC(C=C*1([C@@]2C(F)=C(CO)[C@@]3O)[C@]23O)=NC1=O 0.000 description 1
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 description 1
- 230000001640 apoptogenic effect Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562173174P | 2015-06-09 | 2015-06-09 | |
| US62/173,174 | 2015-06-09 | ||
| US201562210708P | 2015-08-27 | 2015-08-27 | |
| US62/210,708 | 2015-08-27 | ||
| US201662289801P | 2016-02-01 | 2016-02-01 | |
| US62/289,801 | 2016-02-01 | ||
| US201662319369P | 2016-04-07 | 2016-04-07 | |
| US62/319,369 | 2016-04-07 | ||
| PCT/US2016/036768 WO2016201146A1 (en) | 2015-06-09 | 2016-06-09 | Fluorocyclopentenylcytosine uses and processes of preparation |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020190164A Division JP2021042220A (ja) | 2015-06-09 | 2020-11-16 | フルオロシクロペンテニルシトシンの使用および調製のプロセス |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2018516947A JP2018516947A (ja) | 2018-06-28 |
| JP2018516947A5 true JP2018516947A5 (enExample) | 2019-07-04 |
Family
ID=56134700
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017563544A Withdrawn JP2018516947A (ja) | 2015-06-09 | 2016-06-09 | フルオロシクロペンテニルシトシンの使用および調製のプロセス |
| JP2020190164A Pending JP2021042220A (ja) | 2015-06-09 | 2020-11-16 | フルオロシクロペンテニルシトシンの使用および調製のプロセス |
| JP2023069173A Pending JP2023093627A (ja) | 2015-06-09 | 2023-04-20 | フルオロシクロペンテニルシトシンの使用および調製のプロセス |
| JP2025108131A Pending JP2025138772A (ja) | 2015-06-09 | 2025-06-26 | フルオロシクロペンテニルシトシンの使用および調製のプロセス |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020190164A Pending JP2021042220A (ja) | 2015-06-09 | 2020-11-16 | フルオロシクロペンテニルシトシンの使用および調製のプロセス |
| JP2023069173A Pending JP2023093627A (ja) | 2015-06-09 | 2023-04-20 | フルオロシクロペンテニルシトシンの使用および調製のプロセス |
| JP2025108131A Pending JP2025138772A (ja) | 2015-06-09 | 2025-06-26 | フルオロシクロペンテニルシトシンの使用および調製のプロセス |
Country Status (11)
| Country | Link |
|---|---|
| US (3) | US9782410B2 (enExample) |
| EP (2) | EP4008321A1 (enExample) |
| JP (4) | JP2018516947A (enExample) |
| KR (1) | KR20180038440A (enExample) |
| CN (1) | CN107750160B (enExample) |
| AU (1) | AU2016276783B2 (enExample) |
| BR (1) | BR112017025742A2 (enExample) |
| CA (2) | CA3219538A1 (enExample) |
| ES (1) | ES2903212T3 (enExample) |
| MX (1) | MX2017015984A (enExample) |
| WO (1) | WO2016201146A1 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA3160553A1 (en) * | 2013-03-15 | 2014-09-18 | Rexahn Pharmaceuticals, Inc. | Process for the preparation of 4-amino-1-((1s,4r,5s)-2-fluoro-4,5-dihydroxy-3-hydroxymethyl-cyclopent-2-enyl)-1h-pyrimidin-2-one |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS567710A (en) | 1979-06-28 | 1981-01-27 | Sansho Seiyaku Kk | Whitening cosmetic |
| EP0188040B1 (en) | 1985-01-11 | 1991-08-14 | Abbott Laboratories Limited | Slow release solid preparation |
| JP2773959B2 (ja) | 1990-07-10 | 1998-07-09 | 信越化学工業株式会社 | 大腸内放出性固形製剤 |
| UA73092C2 (uk) | 1998-07-17 | 2005-06-15 | Брістол-Майерс Сквібб Компані | Таблетка з ентеросолюбільним покриттям і спосіб її приготування |
| KR100501022B1 (ko) | 1998-07-28 | 2005-07-18 | 다나베 세이야꾸 가부시키가이샤 | 장내 적소 방출형 제제 |
| IN2014DN04587A (enExample) | 2004-04-01 | 2015-07-10 | Rexahn Corp | |
| EP2785375B1 (en) * | 2011-11-28 | 2020-07-22 | Merck Patent GmbH | Anti-pd-l1 antibodies and uses thereof |
| CA3160553A1 (en) | 2013-03-15 | 2014-09-18 | Rexahn Pharmaceuticals, Inc. | Process for the preparation of 4-amino-1-((1s,4r,5s)-2-fluoro-4,5-dihydroxy-3-hydroxymethyl-cyclopent-2-enyl)-1h-pyrimidin-2-one |
| JOP20200094A1 (ar) * | 2014-01-24 | 2017-06-16 | Dana Farber Cancer Inst Inc | جزيئات جسم مضاد لـ pd-1 واستخداماتها |
-
2016
- 2016-06-09 AU AU2016276783A patent/AU2016276783B2/en active Active
- 2016-06-09 CA CA3219538A patent/CA3219538A1/en active Pending
- 2016-06-09 EP EP21203072.0A patent/EP4008321A1/en active Pending
- 2016-06-09 JP JP2017563544A patent/JP2018516947A/ja not_active Withdrawn
- 2016-06-09 CN CN201680034667.0A patent/CN107750160B/zh not_active Expired - Fee Related
- 2016-06-09 WO PCT/US2016/036768 patent/WO2016201146A1/en not_active Ceased
- 2016-06-09 US US15/178,390 patent/US9782410B2/en active Active
- 2016-06-09 BR BR112017025742-4A patent/BR112017025742A2/pt not_active Application Discontinuation
- 2016-06-09 MX MX2017015984A patent/MX2017015984A/es unknown
- 2016-06-09 EP EP16730210.8A patent/EP3307251B8/en active Active
- 2016-06-09 ES ES16730210T patent/ES2903212T3/es active Active
- 2016-06-09 CA CA2986703A patent/CA2986703A1/en active Pending
- 2016-06-09 KR KR1020187000447A patent/KR20180038440A/ko not_active Withdrawn
-
2017
- 2017-08-22 US US15/683,408 patent/US10278971B2/en active Active
-
2019
- 2019-03-18 US US16/356,328 patent/US20190275042A1/en not_active Abandoned
-
2020
- 2020-11-16 JP JP2020190164A patent/JP2021042220A/ja active Pending
-
2023
- 2023-04-20 JP JP2023069173A patent/JP2023093627A/ja active Pending
-
2025
- 2025-06-26 JP JP2025108131A patent/JP2025138772A/ja active Pending
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