TWI622595B - 充當抗癌劑的經取代核苷衍生物 - Google Patents
充當抗癌劑的經取代核苷衍生物 Download PDFInfo
- Publication number
- TWI622595B TWI622595B TW105104968A TW105104968A TWI622595B TW I622595 B TWI622595 B TW I622595B TW 105104968 A TW105104968 A TW 105104968A TW 105104968 A TW105104968 A TW 105104968A TW I622595 B TWI622595 B TW I622595B
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- Taiwan
- Prior art keywords
- cancer
- mmol
- compound
- methyl
- etoac
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- AQGOZRKFBKEVFZ-ZHALLVOQSA-N CCOCc1n[nH]c(C[C@H]([C@H]([C@H]([n]2c3ncnc(C)c3cc2)[O]=C=C)O)O)c1 Chemical compound CCOCc1n[nH]c(C[C@H]([C@H]([C@H]([n]2c3ncnc(C)c3cc2)[O]=C=C)O)O)c1 AQGOZRKFBKEVFZ-ZHALLVOQSA-N 0.000 description 1
- DJUZHNZMVHIRPJ-ZGAAAFHUSA-N C[C@@H]([C@H]([C@H]([C@H]1O)O)O[C@H]1[n]1c(ncnc2N)c2nc1)O Chemical compound C[C@@H]([C@H]([C@H]([C@H]1O)O)O[C@H]1[n]1c(ncnc2N)c2nc1)O DJUZHNZMVHIRPJ-ZGAAAFHUSA-N 0.000 description 1
- ZBUYPOCFIPAVOZ-WXXHYUIPSA-N C[C@H]([C@H]([C@H]([C@H]([n]1c2ncnc(C)c2cc1)O)O)O)[C@H](c1ccccc1)O Chemical compound C[C@H]([C@H]([C@H]([C@H]([n]1c2ncnc(C)c2cc1)O)O)O)[C@H](c1ccccc1)O ZBUYPOCFIPAVOZ-WXXHYUIPSA-N 0.000 description 1
- DJUZHNZMVHIRPJ-RWONEVQGSA-N C[C@H]([C@H]([C@H]([C@H]1O)O)O[C@H]1[n]1c2ncnc(N)c2nc1)O Chemical compound C[C@H]([C@H]([C@H]([C@H]1O)O)O[C@H]1[n]1c2ncnc(N)c2nc1)O DJUZHNZMVHIRPJ-RWONEVQGSA-N 0.000 description 1
- GNLMRHGPHSVOJQ-QSJFSLAZSA-N Cc1c(cc[n]2[C@@H]([C@@H]([C@@H]3O)O)O[C@@H]3C(c(cc3)ccc3F)(F)F)c2ncn1 Chemical compound Cc1c(cc[n]2[C@@H]([C@@H]([C@@H]3O)O)O[C@@H]3C(c(cc3)ccc3F)(F)F)c2ncn1 GNLMRHGPHSVOJQ-QSJFSLAZSA-N 0.000 description 1
- VVNQYJYZOIRSRC-HLNWXESRSA-N Cc1c(cc[n]2[C@@H]([C@@H]([C@@H]3O)O)O[C@H]3c(cc3)n[n]3-c3ccccc3)c2ncn1 Chemical compound Cc1c(cc[n]2[C@@H]([C@@H]([C@@H]3O)O)O[C@H]3c(cc3)n[n]3-c3ccccc3)c2ncn1 VVNQYJYZOIRSRC-HLNWXESRSA-N 0.000 description 1
- XREICMJCVZYTAR-CGKSDVGLSA-N Cc1c(cc[n]2[C@@H]([C@@H]3O)OC(C(c4cc(F)cc(C(F)(F)F)c4)O)[C@H]3O)c2ncn1 Chemical compound Cc1c(cc[n]2[C@@H]([C@@H]3O)OC(C(c4cc(F)cc(C(F)(F)F)c4)O)[C@H]3O)c2ncn1 XREICMJCVZYTAR-CGKSDVGLSA-N 0.000 description 1
- RASMCBDASZAHRP-RIUYPTKQSA-N Cc1c(cc[n]2[C@@H]([C@@H]3O)O[C@@H]([C@@H](c(cc4)ccc4F)O)[C@H]3O)c2ncn1 Chemical compound Cc1c(cc[n]2[C@@H]([C@@H]3O)O[C@@H]([C@@H](c(cc4)ccc4F)O)[C@H]3O)c2ncn1 RASMCBDASZAHRP-RIUYPTKQSA-N 0.000 description 1
- CJOLNWSXRHCRGA-RIUYPTKQSA-N Cc1c(cc[n]2[C@@H]([C@@H]3O)O[C@@H]([C@@H](c4ccccc4)O)[C@H]3O)c2ncn1 Chemical compound Cc1c(cc[n]2[C@@H]([C@@H]3O)O[C@@H]([C@@H](c4ccccc4)O)[C@H]3O)c2ncn1 CJOLNWSXRHCRGA-RIUYPTKQSA-N 0.000 description 1
- RASMCBDASZAHRP-RNGZQALNSA-N Cc1c(cc[n]2[C@@H]([C@@H]3O)O[C@@H]([C@H](c(cc4)ccc4F)O)[C@H]3O)c2ncn1 Chemical compound Cc1c(cc[n]2[C@@H]([C@@H]3O)O[C@@H]([C@H](c(cc4)ccc4F)O)[C@H]3O)c2ncn1 RASMCBDASZAHRP-RNGZQALNSA-N 0.000 description 1
- JJSRCFYJJKHXSP-FSNPWBFUSA-N Cc1c(cc[n]2[C@@H]([C@@H]3O)O[C@H]([C@@H](c4cc(N(C)C)ncc4)O)[C@H]3O)c2ncn1 Chemical compound Cc1c(cc[n]2[C@@H]([C@@H]3O)O[C@H]([C@@H](c4cc(N(C)C)ncc4)O)[C@H]3O)c2ncn1 JJSRCFYJJKHXSP-FSNPWBFUSA-N 0.000 description 1
- DQMAAYMQZKAQJY-FSNPWBFUSA-N Cc1ncnc2c1cc[n]2[C@@H]([C@@H]1O)O[C@H]([C@@H](c(cc2)cc3c2[n](C(F)F)cn3)O)[C@H]1O Chemical compound Cc1ncnc2c1cc[n]2[C@@H]([C@@H]1O)O[C@H]([C@@H](c(cc2)cc3c2[n](C(F)F)cn3)O)[C@H]1O DQMAAYMQZKAQJY-FSNPWBFUSA-N 0.000 description 1
- LOOUVRBRGOENGZ-FSNPWBFUSA-N Cc1ncnc2c1cc[n]2[C@@H]([C@@H]1O)O[C@H]([C@@H](c(cc2)cc3c2nc[n]3C(F)F)O)[C@H]1O Chemical compound Cc1ncnc2c1cc[n]2[C@@H]([C@@H]1O)O[C@H]([C@@H](c(cc2)cc3c2nc[n]3C(F)F)O)[C@H]1O LOOUVRBRGOENGZ-FSNPWBFUSA-N 0.000 description 1
- WNGZPIOXKRMXPJ-ORDFZIBCSA-N Cc1ncnc2c1cc[n]2[C@@H]([C@@H]1O)O[C@H]([C@@H](c2cccc(C(F)(F)F)c2)O)[C@H]1O Chemical compound Cc1ncnc2c1cc[n]2[C@@H]([C@@H]1O)O[C@H]([C@@H](c2cccc(C(F)(F)F)c2)O)[C@H]1O WNGZPIOXKRMXPJ-ORDFZIBCSA-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)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Oncology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Peptides Or Proteins (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (6)
| 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201643176A TW201643176A (zh) | 2016-12-16 |
| TWI622595B true TWI622595B (zh) | 2018-05-01 |
Family
ID=55451515
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW105104968A TWI622595B (zh) | 2015-02-24 | 2016-02-19 | 充當抗癌劑的經取代核苷衍生物 |
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=) |
Families Citing this family (43)
| 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 |
| PE20181894A1 (es) | 2016-03-10 | 2018-12-11 | Janssen Pharmaceutica Nv | Nuevos analogos de nucleosidos sustituidos para su uso como inhibidores de prmt 5 |
| TN2018000310A1 (en) | 2016-03-10 | 2020-01-16 | Janssen Pharmaceutica Nv | Substituted nucleoside analogues for use as prmt5 inhibitors |
| MA46228A (fr) | 2016-09-14 | 2019-07-24 | Janssen Pharmaceutica Nv | Inhibiteurs bicycliques fusionnés de l'interaction ménine-mll |
| US12084462B2 (en) | 2016-09-14 | 2024-09-10 | Janssen Pharmaceutica Nv | Spiro bicyclic inhibitors of menin-MLL interaction |
| CN109689663B (zh) | 2016-09-14 | 2023-04-14 | 詹森药业有限公司 | Menin-mll相互作用的螺二环抑制剂 |
| CN115626935B (zh) * | 2016-10-03 | 2025-07-15 | 詹森药业有限公司 | 用作prmt5抑制剂的单环和双环系统取代的卡巴核苷类似物 |
| BR112019012106A2 (pt) | 2016-12-15 | 2019-10-29 | Janssen Pharmaceutica Nv | inibidores de azepano de interação menin-mill |
| WO2018152501A1 (en) * | 2017-02-20 | 2018-08-23 | Prelude Therapeutics, Incorporated | Selective inhibitors of protein arginine methyltransferase 5 (prmt5) |
| WO2018152548A1 (en) * | 2017-02-20 | 2018-08-23 | Prelude Therapeutics, Incorporated | Selective inhibitors of protein arginine methyltransferase 5 (prmt5) |
| EA201990851A1 (ru) | 2017-02-24 | 2019-09-30 | Янссен Фармацевтика Нв | Новые аналоги карбануклеозида, замещенные моноциклической и бициклической кольцевой системой, для применения в качестве ингибиторов prmt5 |
| CN110382707A (zh) | 2017-02-27 | 2019-10-25 | 詹森药业有限公司 | 生物标志在鉴定将对用prmt5抑制剂治疗有响应的癌症患者中的用途 |
| WO2018160855A1 (en) | 2017-03-01 | 2018-09-07 | Prelude Therapeutics, Incorporated | Selective inhibitors of protein arginine methyltransferase 5 (prmt5) |
| PL3665179T3 (pl) * | 2017-08-09 | 2021-11-29 | Prelude Therapeutics, Incorporated | Selektywne inhibitory metylotransferazy argininowej białek 5 (prmt5) |
| WO2019084470A1 (en) * | 2017-10-26 | 2019-05-02 | Prelude Therapeutics, Incorporated | SELECTIVE INHIBITORS OF THE PROTEIN ARGININE METHYLTRANSFERASE 5 (PRMT5) |
| IL275129B2 (en) * | 2017-12-08 | 2023-10-01 | Janssen Pharmaceutica Nv | Novel spirobicyclic analogues |
| HUE059945T2 (hu) | 2017-12-13 | 2023-01-28 | Lupin Ltd | Helyettesített biciklusos heterociklusos vegyületek, mint PRMT5 inhibitorok |
| US11396517B1 (en) | 2017-12-20 | 2022-07-26 | Janssen Pharmaceutica Nv | Exo-aza spiro inhibitors of menin-MLL interaction |
| US10711007B2 (en) | 2018-03-14 | 2020-07-14 | Prelude Therapeutics Incorporated | Selective inhibitors of protein arginine methyltransferase 5 (PRMT5) |
| BR112020018636A2 (pt) * | 2018-03-14 | 2020-12-29 | Prelude Therapeutics, Incorporated | Inibidores seletivos de proteína arginina metiltransferase 5 (prmt5) |
| GB201810092D0 (en) | 2018-06-20 | 2018-08-08 | Ctxt Pty Ltd | Compounds |
| EP3833669A4 (en) * | 2018-08-07 | 2022-05-11 | Merck Sharp & Dohme Corp. | PRMT5 INHIBITORS |
| AU2020223058A1 (en) * | 2019-02-13 | 2021-09-09 | Prelude Therapeutics, Incorporated | Selective inhibitor of protein arginine methyltransferase 5 (PRMT5) |
| EP3947387B1 (en) * | 2019-03-25 | 2024-10-23 | California Institute Of Technology | Prmt5 inhibitors and uses thereof |
| WO2020206299A1 (en) | 2019-04-05 | 2020-10-08 | Prelude Therapeutics, Incorporated | Selective inhibitors of protein arginine methyltransferase 5 |
| 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 |
| PL3980417T3 (pl) | 2019-06-10 | 2024-03-18 | Lupin Limited | Inhibitory prmt5 |
| JP7598338B2 (ja) | 2019-06-12 | 2024-12-11 | ヤンセン ファーマシューティカ エヌ．ベー． | 新規なスピロ二環式中間体 |
| KR102823056B1 (ko) | 2019-06-18 | 2025-06-23 | 화이자 인코포레이티드 | 벤즈이속사졸 설폰아마이드 유도체 |
| WO2021055797A1 (en) * | 2019-09-18 | 2021-03-25 | Prelude Therapeutics, Incorporated | Selective inhibitors of protein arginine methyltransferase 5 (prmt5) |
| UA128683C2 (uk) | 2019-10-22 | 2024-09-25 | Люпін Лімітед | Фармацевтична комбінація на основі інгібіторів prmt5 |
| US20230066014A1 (en) | 2019-12-03 | 2023-03-02 | Lupin Limited | Substituted nucleoside analogs as prmt5 inhibitors |
| JP7554829B2 (ja) | 2019-12-19 | 2024-09-20 | ヤンセン ファーマシューティカ エヌ．ベー． | 置換直鎖スピロ誘導体 |
| CA3192099A1 (en) | 2020-08-18 | 2022-02-24 | Incyte Corporation | Process and intermediates for preparing a jak inhibitor |
| CR20230130A (es) | 2020-08-18 | 2023-07-13 | Incyte Corp | Proceso e intermedios para preparar un inhibidor de jak1 |
| US20240101589A1 (en) * | 2020-10-08 | 2024-03-28 | Strom Therapeutics Limited | Inhibitors of mettl3 |
| CN112679505B (zh) * | 2020-12-25 | 2022-04-22 | 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 |
| WO2022153161A1 (en) | 2021-01-14 | 2022-07-21 | Pfizer Inc. | Treatment of cancer using a prmt5 inhibitor |
| CN118317946A (zh) | 2021-07-12 | 2024-07-09 | 因赛特公司 | 用于制备巴瑞替尼的方法和中间体 |
| EP4384519A1 (en) * | 2021-08-13 | 2024-06-19 | 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 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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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 |
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