CN107278205A - 用作抗癌药的取代的核苷衍生物 - Google Patents
用作抗癌药的取代的核苷衍生物 Download PDFInfo
- Publication number
- CN107278205A CN107278205A CN201680011823.1A CN201680011823A CN107278205A CN 107278205 A CN107278205 A CN 107278205A CN 201680011823 A CN201680011823 A CN 201680011823A CN 107278205 A CN107278205 A CN 107278205A
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- China
- Prior art keywords
- alkyl
- hydrogen
- hydroxyl
- cancer
- aryl
- 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.)
- Pending
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- 0 CC(C)C[C@@]([C@@](*)[C@]([C@@](*)C[C@]([n]1c(N=CCC=C2N)c2nc1)O)O)N Chemical compound CC(C)C[C@@]([C@@](*)[C@]([C@@](*)C[C@]([n]1c(N=CCC=C2N)c2nc1)O)O)N 0.000 description 21
- QWIAHMVNMONKCU-UHFFFAOYSA-N Cc1ncnc2c1cc[nH]2 Chemical compound Cc1ncnc2c1cc[nH]2 QWIAHMVNMONKCU-UHFFFAOYSA-N 0.000 description 3
- CZMLCMOUGCMWFA-PLNGDYQASA-N C/C=C\c1c(C)ncnc1C Chemical compound C/C=C\c1c(C)ncnc1C CZMLCMOUGCMWFA-PLNGDYQASA-N 0.000 description 1
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- BLFJUWOUOPYDHP-XQVHRTOBSA-N C[C@@H](C1OC(C)CC1)c(cc1)cc(F)c1F Chemical compound C[C@@H](C1OC(C)CC1)c(cc1)cc(F)c1F BLFJUWOUOPYDHP-XQVHRTOBSA-N 0.000 description 1
- ZWPYBFJDYDLLJD-WGLFHAEBSA-N C[C@@H](CC1)OC1[C@@H](c(cc1)cc(F)c1F)F Chemical compound C[C@@H](CC1)OC1[C@@H](c(cc1)cc(F)c1F)F ZWPYBFJDYDLLJD-WGLFHAEBSA-N 0.000 description 1
- ARTCXJGCMYSPSV-LWXNQMLSSA-N C[C@@H]([C@H]([C@H]([C@H]([n](cc1)c2c1c(C)ncn2)O)[O]#C)O)[C@@H](c1ccnc(N(C)C)c1)O Chemical compound C[C@@H]([C@H]([C@H]([C@H]([n](cc1)c2c1c(C)ncn2)O)[O]#C)O)[C@@H](c1ccnc(N(C)C)c1)O ARTCXJGCMYSPSV-LWXNQMLSSA-N 0.000 description 1
- ZQGBYLVSLUPNJY-DPZFQJAZSA-N C[C@@H]([C@H]([C@H]([C@H]([n]1c2nc(N)nc(C)c2cc1)O)O)O)[C@@H](c(cc1)cc(F)c1Cl)O Chemical compound C[C@@H]([C@H]([C@H]([C@H]([n]1c2nc(N)nc(C)c2cc1)O)O)O)[C@@H](c(cc1)cc(F)c1Cl)O ZQGBYLVSLUPNJY-DPZFQJAZSA-N 0.000 description 1
- BLPNMFYSTXNPRA-CELJHQOASA-N C[C@@H]([C@H]([C@H]([C@H]1O)[O]#C)O[C@H]1[n]1c(CN=CN=C(C2)N=C)c2nc1)O Chemical compound C[C@@H]([C@H]([C@H]([C@H]1O)[O]#C)O[C@H]1[n]1c(CN=CN=C(C2)N=C)c2nc1)O BLPNMFYSTXNPRA-CELJHQOASA-N 0.000 description 1
- PKKNCXMMSQGGEH-RWONEVQGSA-N C[C@H]([C@H]([C@H]([C@H]1O)O)O[C@H]1[n]1c(N=CN=[IH]=C2N)c2nc1)O Chemical compound C[C@H]([C@H]([C@H]([C@H]1O)O)O[C@H]1[n]1c(N=CN=[IH]=C2N)c2nc1)O PKKNCXMMSQGGEH-RWONEVQGSA-N 0.000 description 1
- CGWYOBCRCVTPCD-DLBZAZTESA-N Cc1c(cc[n]2[C@@H](CCC[C@@H](c(cc3)ccc3F)O)O)c2ncn1 Chemical compound Cc1c(cc[n]2[C@@H](CCC[C@@H](c(cc3)ccc3F)O)O)c2ncn1 CGWYOBCRCVTPCD-DLBZAZTESA-N 0.000 description 1
- CGWYOBCRCVTPCD-IAGOWNOFSA-N Cc1c(cc[n]2[C@@H](CCC[C@H](c(cc3)ccc3F)O)O)c2ncn1 Chemical compound Cc1c(cc[n]2[C@@H](CCC[C@H](c(cc3)ccc3F)O)O)c2ncn1 CGWYOBCRCVTPCD-IAGOWNOFSA-N 0.000 description 1
- UPZRLNSBZRVUAI-RUINGEJQSA-N Cc1ncnc2c1cc[n]2CC(CC1)O[C@@H]1C(c(cc1)cc(F)c1F)=O Chemical compound Cc1ncnc2c1cc[n]2CC(CC1)O[C@@H]1C(c(cc1)cc(F)c1F)=O UPZRLNSBZRVUAI-RUINGEJQSA-N 0.000 description 1
- BPTCCCTWWAUJRK-UHFFFAOYSA-N Clc1c(cc[nH]2)c2ncn1 Chemical compound Clc1c(cc[nH]2)c2ncn1 BPTCCCTWWAUJRK-UHFFFAOYSA-N 0.000 description 1
- KOJURFLWNZUGAX-JTRQHRHOSA-N N[C@@H](C(C[C@H]1O)O[C@H]1[n](cc1)c2c1cncn2)c(cc1)cc(F)c1F Chemical compound N[C@@H](C(C[C@H]1O)O[C@H]1[n](cc1)c2c1cncn2)c(cc1)cc(F)c1F KOJURFLWNZUGAX-JTRQHRHOSA-N 0.000 description 1
- PEHVGBZKEYRQSX-UHFFFAOYSA-N Nc1ncnc2c1cc[nH]2 Chemical compound Nc1ncnc2c1cc[nH]2 PEHVGBZKEYRQSX-UHFFFAOYSA-N 0.000 description 1
- WSJHYNQJBOXITQ-JTTNIQEDSA-N O[C@@H]([C@H]([C@H]([C@H]1O)O)O[C@H]1[n]1c2nc(Cl)ncc2c(F)c1)c(cc1F)ccc1F Chemical compound O[C@@H]([C@H]([C@H]([C@H]1O)O)O[C@H]1[n]1c2nc(Cl)ncc2c(F)c1)c(cc1F)ccc1F WSJHYNQJBOXITQ-JTTNIQEDSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/14—Pyrrolo-pyrimidine radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
- A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
- C07H19/167—Purine radicals with ribosyl as the saccharide radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/23—Heterocyclic radicals containing two or more heterocyclic rings condensed among themselves or condensed with a common carbocyclic ring system, not provided for in groups C07H19/14 - C07H19/22
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/24—Heterocyclic radicals containing oxygen or sulfur as ring hetero atom
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Peptides Or Proteins (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562119932P | 2015-02-24 | 2015-02-24 | |
| US62/119,932 | 2015-02-24 | ||
| US201562213801P | 2015-09-03 | 2015-09-03 | |
| US62/213,801 | 2015-09-03 | ||
| US201662279209P | 2016-01-15 | 2016-01-15 | |
| US62/279,209 | 2016-01-15 | ||
| PCT/IB2016/050803 WO2016135582A1 (en) | 2015-02-24 | 2016-02-15 | Substituted nucleoside derivatives useful as anticancer agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN107278205A true CN107278205A (zh) | 2017-10-20 |
Family
ID=55451515
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201680011823.1A Pending CN107278205A (zh) | 2015-02-24 | 2016-02-15 | 用作抗癌药的取代的核苷衍生物 |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US10428104B2 (https=) |
| EP (1) | EP3262057B1 (https=) |
| JP (1) | JP6584521B2 (https=) |
| KR (1) | KR20170119705A (https=) |
| CN (1) | CN107278205A (https=) |
| AU (2) | AU2016225133B2 (https=) |
| BR (1) | BR112017017396A2 (https=) |
| CA (1) | CA2921314A1 (https=) |
| CL (1) | CL2017002155A1 (https=) |
| CO (1) | CO2017008403A2 (https=) |
| CR (1) | CR20170384A (https=) |
| CU (1) | CU20170105A7 (https=) |
| DO (1) | DOP2017000195A (https=) |
| EA (1) | EA031895B1 (https=) |
| ES (1) | ES2792899T3 (https=) |
| GT (1) | GT201700189A (https=) |
| IL (1) | IL253637A0 (https=) |
| MX (1) | MX2017010844A (https=) |
| NI (1) | NI201700095A (https=) |
| PE (1) | PE20171449A1 (https=) |
| PH (1) | PH12017501413A1 (https=) |
| SG (1) | SG11201706050WA (https=) |
| SV (1) | SV2017005514A (https=) |
| TN (1) | TN2017000357A1 (https=) |
| TW (1) | TWI622595B (https=) |
| UA (1) | UA118315C2 (https=) |
| UY (1) | UY36564A (https=) |
| WO (1) | WO2016135582A1 (https=) |
| ZA (1) | ZA201705092B (https=) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111542525A (zh) * | 2017-10-26 | 2020-08-14 | 普莱鲁德疗法有限公司 | 蛋白质精氨酸甲基转移酶5(prmt5)的选择性抑制剂 |
| CN112679505A (zh) * | 2020-12-25 | 2021-04-20 | 杭州澳赛诺生物科技有限公司 | 一种4-甲基-7H-吡咯并[2,3-d]嘧啶的合成方法 |
| CN114127072A (zh) * | 2019-03-25 | 2022-03-01 | 加利福尼亚技术学院 | Prmt5抑制剂及其用途 |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR104326A1 (es) * | 2015-05-04 | 2017-07-12 | Lilly Co Eli | Compuestos nucleósidos 5-sustituidos |
| TWI870767B (zh) | 2015-08-26 | 2025-01-21 | 比利時商健生藥品公司 | 使用作為prmt5抑制劑之新穎經6-6雙環芳香環取代之核苷類似物 |
| US10898504B2 (en) | 2016-03-10 | 2021-01-26 | Janssen Pharmaceutica Nv | Substituted nucleoside analogues for use as PRMT5 inhibitors |
| AU2017230658B2 (en) | 2016-03-10 | 2021-03-04 | Janssen Pharmaceutica Nv | Substituted nucleoside analogues for use as PRMT5 inhibitors |
| US12084462B2 (en) | 2016-09-14 | 2024-09-10 | Janssen Pharmaceutica Nv | Spiro bicyclic inhibitors of menin-MLL interaction |
| CA3033020A1 (en) | 2016-09-14 | 2018-03-22 | Janssen Pharmaceutica Nv | Fused bicyclic inhibitors of menin-mll interaction |
| EP3512857B1 (en) | 2016-09-14 | 2021-02-24 | Janssen Pharmaceutica NV | Spiro bicyclic inhibitors of menin-mll interaction |
| TN2019000087A1 (en) | 2016-10-03 | 2020-07-15 | Janssen Pharmaceutica Nv | Novel monocyclic and bicyclic ring system substituted carbanucleoside analogues for use as prmt5 inhibitors |
| WO2018065365A1 (en) | 2016-10-03 | 2018-04-12 | Janssen Pharmaceutica Nv | Novel monocyclic and bicyclic ring system substituted carbanucleoside analogues for use as prmt5 inhibitors |
| CN110248946B (zh) | 2016-12-15 | 2023-05-23 | 詹森药业有限公司 | Menin-MLL相互作用的氮杂环庚烷抑制剂 |
| US11220524B2 (en) * | 2017-02-20 | 2022-01-11 | Prelude Therapeutics Incorporated | Selective inhibitors of protein arginine methyltransferase 5 (PRMT5) |
| WO2018152501A1 (en) * | 2017-02-20 | 2018-08-23 | Prelude Therapeutics, Incorporated | Selective inhibitors of protein arginine methyltransferase 5 (prmt5) |
| TN2019000212A1 (en) | 2017-02-27 | 2021-01-07 | Janssen Pharmaceutica Nv | Use of biomarkers in identifying cancer patients that will be responsive to treatment with a prmt5 inhibitor |
| WO2018160855A1 (en) | 2017-03-01 | 2018-09-07 | Prelude Therapeutics, Incorporated | Selective inhibitors of protein arginine methyltransferase 5 (prmt5) |
| EP3939986A1 (en) | 2017-08-09 | 2022-01-19 | Prelude Therapeutics, Incorporated | Selective inhibitors of protein arginine methyltransferase 5 (prmt5) |
| US11059850B2 (en) | 2017-12-08 | 2021-07-13 | Janssen Pharmaceutica Nv | Spirobicyclic analogues |
| SMT202200396T1 (it) | 2017-12-13 | 2022-11-18 | Lupin Ltd | Composti eterociclici biciclici sostituiti come inibitori di prmt5 |
| US11396517B1 (en) | 2017-12-20 | 2022-07-26 | Janssen Pharmaceutica Nv | Exo-aza spiro inhibitors of menin-MLL interaction |
| AU2019235912B2 (en) * | 2018-03-14 | 2024-03-21 | Prelude Therapeutics, Incorporated | Selective inhibitors of protein arginine methyltransferase 5 (PRMT5) |
| US10711007B2 (en) | 2018-03-14 | 2020-07-14 | Prelude Therapeutics Incorporated | Selective inhibitors of protein arginine methyltransferase 5 (PRMT5) |
| GB201810092D0 (en) | 2018-06-20 | 2018-08-08 | Ctxt Pty Ltd | Compounds |
| US12552826B2 (en) | 2018-08-07 | 2026-02-17 | Merck Sharp & Dohme Llc | PRMT5 inhibitors |
| EP3924360A1 (en) * | 2019-02-13 | 2021-12-22 | Prelude Therapeutics, Incorporated | Selective inhibitor of protein arginine methyltransferase 5 (prmt5) |
| JP2022526604A (ja) | 2019-04-05 | 2022-05-25 | プレリュード・セラピューティクス・インコーポレイテッド | タンパク質アルギニンメチルトランスフェラーゼ５の選択的阻害剤 |
| TW202112375A (zh) | 2019-06-06 | 2021-04-01 | 比利時商健生藥品公司 | 使用ｐｒｍｔ５抑制劑治療癌症之方法 |
| HUE064493T2 (hu) | 2019-06-10 | 2024-03-28 | Lupin Ltd | PRMT5 inhibitorok |
| KR20220019766A (ko) | 2019-06-12 | 2022-02-17 | 얀센 파마슈티카 엔.브이. | 신규 스피로바이사이클릭 중간체 |
| DK4299135T3 (da) | 2019-06-18 | 2025-09-08 | Pfizer | Benzisoxazol-sulfonamid-derivater |
| WO2021055797A1 (en) * | 2019-09-18 | 2021-03-25 | Prelude Therapeutics, Incorporated | Selective inhibitors of protein arginine methyltransferase 5 (prmt5) |
| KR20220086628A (ko) | 2019-10-22 | 2022-06-23 | 루핀 리미티드 | Prmt5 저해제의 약학적 조합물 |
| EP4069698A1 (en) | 2019-12-03 | 2022-10-12 | Lupin Limited | Substituted nucleoside analogs as prmt5 inhibitors |
| TW202525813A (zh) | 2019-12-19 | 2025-07-01 | 比利時商健生藥品公司 | 經取代之直鏈螺環接衍生物 |
| PE20231743A1 (es) | 2020-08-18 | 2023-10-31 | Incyte Corp | Proceso e intermediarios para preparar un inhibidor de jak |
| IL300557A (en) | 2020-08-18 | 2023-04-01 | Incyte Corp | Process and intermediates for preparing a JAK1 inhibitor |
| WO2022074391A1 (en) * | 2020-10-08 | 2022-04-14 | Storm Therapeutics Limited | Compounds inhibitors of mettl3 |
| WO2022153161A1 (en) | 2021-01-14 | 2022-07-21 | Pfizer Inc. | Treatment of cancer using a prmt5 inhibitor |
| US12071439B2 (en) | 2021-07-12 | 2024-08-27 | Incyte Corporation | Process and intermediates for preparing a JAK inhibitor |
| US20250188110A1 (en) * | 2021-08-13 | 2025-06-12 | Albert-Ludwigs-Universität Freiburg | Specific small molecule inhibitors that block kmt9 methyltransferase activity and function |
| WO2024170488A1 (en) | 2023-02-13 | 2024-08-22 | Astrazeneca Ab | Prmt5 inhibitor for use in cancer therapy |
| WO2026008533A1 (en) | 2024-07-01 | 2026-01-08 | Janssen Pharmaceutica Nv | Prmt5 inhibitors for treating adenomas |
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| US6492348B1 (en) * | 1998-06-23 | 2002-12-10 | Smithkline Beecham Corporation | Adenosine derivatives |
| US20040043960A1 (en) * | 2002-08-15 | 2004-03-04 | Jeff Zablocki | Partial and full agonists of A1 adenosine receptors |
| CN107580602A (zh) * | 2015-05-04 | 2018-01-12 | 伊莱利利公司 | 5’‑取代的核苷类似物 |
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| US5646128A (en) * | 1989-09-15 | 1997-07-08 | Gensia, Inc. | Methods for treating adenosine kinase related conditions |
| US5864033A (en) * | 1989-09-15 | 1999-01-26 | Metabasis Therapeutics, Inc. | Adenosine kinase inhibitors |
| US5795977A (en) * | 1989-09-15 | 1998-08-18 | Metabasis Therapeutics, Inc. | Water soluble adenosine kinase inhibitors |
| US5376645A (en) | 1990-01-23 | 1994-12-27 | University Of Kansas | Derivatives of cyclodextrins exhibiting enhanced aqueous solubility and the use thereof |
| KR0166088B1 (ko) | 1990-01-23 | 1999-01-15 | . | 수용해도가 증가된 시클로덱스트린 유도체 및 이의 용도 |
| GB9518953D0 (en) | 1995-09-15 | 1995-11-15 | Pfizer Ltd | Pharmaceutical formulations |
| WO2000035296A1 (en) | 1996-11-27 | 2000-06-22 | Wm. Wrigley Jr. Company | Improved release of medicament active agents from a chewing gum coating |
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| CN111542525A (zh) * | 2017-10-26 | 2020-08-14 | 普莱鲁德疗法有限公司 | 蛋白质精氨酸甲基转移酶5(prmt5)的选择性抑制剂 |
| CN111542525B (zh) * | 2017-10-26 | 2023-06-27 | 普莱鲁德疗法有限公司 | 蛋白质精氨酸甲基转移酶5(prmt5)的选择性抑制剂 |
| CN114127072A (zh) * | 2019-03-25 | 2022-03-01 | 加利福尼亚技术学院 | Prmt5抑制剂及其用途 |
| CN114127072B (zh) * | 2019-03-25 | 2024-10-11 | 加利福尼亚技术学院 | Prmt5抑制剂及其用途 |
| CN112679505A (zh) * | 2020-12-25 | 2021-04-20 | 杭州澳赛诺生物科技有限公司 | 一种4-甲基-7H-吡咯并[2,3-d]嘧啶的合成方法 |
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