PE20231295A1 - Inhibidores de prmt5 - Google Patents
Inhibidores de prmt5Info
- Publication number
- PE20231295A1 PE20231295A1 PE2023001893A PE2023001893A PE20231295A1 PE 20231295 A1 PE20231295 A1 PE 20231295A1 PE 2023001893 A PE2023001893 A PE 2023001893A PE 2023001893 A PE2023001893 A PE 2023001893A PE 20231295 A1 PE20231295 A1 PE 20231295A1
- Authority
- PE
- Peru
- Prior art keywords
- alkyl
- haloalkyl
- halo
- saturated
- naphthyridin
- Prior art date
Links
- 102100034607 Protein arginine N-methyltransferase 5 Human genes 0.000 title abstract 2
- 101710084427 Protein arginine N-methyltransferase 5 Proteins 0.000 title abstract 2
- 239000003112 inhibitor Substances 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 4
- 125000005843 halogen group Chemical group 0.000 abstract 4
- 229910052757 nitrogen Inorganic materials 0.000 abstract 4
- 229920006395 saturated elastomer Polymers 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 abstract 2
- 125000005842 heteroatom Chemical group 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- WRXATAQIIIRZHU-MPBGBICISA-N (4-amino-1,3-dihydrofuro[3,4-c][1,7]naphthyridin-8-yl)-[(3S,5R)-3-(6-cyclopropyloxypyridazin-3-yl)-5-methylmorpholin-4-yl]methanone Chemical compound C[C@H](COC[C@@H]1C(N=N2)=CC=C2OC2CC2)N1C(C(N=C1)=CC(C2=C3COC2)=C1N=C3N)=O WRXATAQIIIRZHU-MPBGBICISA-N 0.000 abstract 1
- HZFPEUSWIDLNSY-GOSISDBHSA-N (4-amino-1-methylpyrazolo[4,3-c][1,7]naphthyridin-8-yl)-[(3S)-3-[4-(trifluoromethyl)phenyl]morpholin-4-yl]methanone Chemical compound CN1N=CC2=C1C(C=C(C(N(CCOC1)[C@H]1C1=CC=C(C(F)(F)F)C=C1)=O)N=C1)=C1N=C2N HZFPEUSWIDLNSY-GOSISDBHSA-N 0.000 abstract 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- 208000019838 Blood disease Diseases 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 208000014951 hematologic disease Diseases 0.000 abstract 1
- 208000018706 hematopoietic system disease Diseases 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 208000030159 metabolic disease Diseases 0.000 abstract 1
- 230000002503 metabolic effect Effects 0.000 abstract 1
- 125000004043 oxo group Chemical group O=* 0.000 abstract 1
- -1 pentafluorosulfanyl Chemical group 0.000 abstract 1
- 230000002062 proliferating effect Effects 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/16—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
- C07D491/147—Ortho-condensed systems the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/16—Peri-condensed systems
Abstract
Un compuesto de Formula I, en donde R1 , R2 y el atomo de nitrogeno al que estan unidos forman un anillo de cinco, seis o siete miembros que puede estar saturado o parcialmente saturado, y comprende 0, 1 o 2 heteroatomos adicionales, iguales o diferentes seleccionados de O, N o S, en donde el atomo de S esta opcionalmente sustituido con uno o dos grupos oxo; en donde el anillo formado por R1 , R2 y el atomo de nitrogeno al que estan unidos puede estar sustituido con 0, 1, 2 o 3 R3 ; en donde R3 se selecciona en cada caso de alquilo C1-6 , halo, haloalquilo C1-6 , -O-alquilo C1-6 , -O-haloalquilo C1-6 , -C(O)-alquilo C1-6 , -C(O)-haloalquilo C1-6 , -C(O)O-alquilo C1-6 , -C(O)Ohaloalquilo C1-6 y ciclo de cinco o seis miembros que puede estar saturado, parcialmente saturado o ser aromatico, y comprende 0, 1 o 2 heteroatomos, iguales o diferentes, seleccionados de O, N y S, en donde el ciclo puede estar opcionalmente sustituido con uno o mas Ra , en donde Ra se selecciona en cada caso de halo, CN, alquilo C1-6 , haloalquilo C1-6 , pentafluorosulfanilo, -O-alquilo C1-3 y -O-haloalquilo C1-3; en donde R es un triciclo seleccionado de las formulas IA y IB; X1 , X2 , X6 , X7 y X8 se seleccionan en cada caso de N y C opcionalmente sustituidos, en donde los sustituyentes se seleccionan de alquilo C1-3; en donde tanto X1 como X2 no pueden ser N al mismo tiempo, y X6 y X7 , y X7 y X8 no pueden ser N al mismo tiempo; ademas en donde si X1 es C, puede estar opcionalmente sustituido con halo; X3 , X4 y X5 se seleccionan en cada caso de C, O, N y S opcionalmente sustituidos, en donde los sustituyentes se seleccionan de alquilo C1-3 y alquil C1-3 (OH), en donde el alquilo puede estar opcionalmente sustituido con halo. Son compuestos preferidos: (4-amino-1-metil-1H-pirazolo[4,3-c][1,7]naftiridin-8-il)((3S)-3-(4-(trifluorometil)fenil)-4- morfolinil)metanona; (4-amino-1,3-dihidrofuro[3,4-c][1,7]naftiridin-8-il)((3S,5R)-3-(6-(ciclopropiloxi)-3- piridazinil)-5-metil-4-morfolinil)metanona; entre otros. Dichos compuestos son utiles para inhibir la actividad de PRMT5 y pueden tener uso en el tratamiento de trastornos proliferativos, metabolicos y sanguineos.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US202063126416P | 2020-12-16 | 2020-12-16 | |
| PCT/US2021/063540 WO2022132914A1 (en) | 2020-12-16 | 2021-12-15 | Prmts inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PE20231295A1 true PE20231295A1 (es) | 2023-08-22 |
Family
ID=79927288
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PE2023001893A PE20231295A1 (es) | 2020-12-16 | 2021-12-15 | Inhibidores de prmt5 |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US11845760B2 (es) |
| EP (1) | EP4263545A1 (es) |
| JP (1) | JP2023550530A (es) |
| KR (1) | KR20230121820A (es) |
| CN (1) | CN116888120A (es) |
| AR (1) | AR124369A1 (es) |
| AU (1) | AU2021400942A1 (es) |
| CA (1) | CA3204823A1 (es) |
| CL (1) | CL2023001738A1 (es) |
| CO (1) | CO2023008167A2 (es) |
| CR (1) | CR20230310A (es) |
| IL (1) | IL303451A (es) |
| MX (1) | MX2023007192A (es) |
| PE (1) | PE20231295A1 (es) |
| TW (1) | TW202233183A (es) |
| UY (1) | UY39565A (es) |
| WO (1) | WO2022132914A1 (es) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2022337201A1 (en) * | 2021-08-30 | 2024-03-07 | Amgen Inc. | Process for synthesizing naphthyridine derivatives and intermediates thereof |
| WO2023196545A1 (en) * | 2022-04-08 | 2023-10-12 | Amgen Inc. | Cancer treatments using mta-cooperative prmt5 inhibitors |
| WO2024002263A1 (zh) * | 2022-06-30 | 2024-01-04 | 南京明德新药研发有限公司 | 氨基取代的杂芳基衍生物及其应用 |
| WO2024002376A1 (zh) * | 2022-07-01 | 2024-01-04 | 上海赛岚生物科技有限公司 | 一类prmt5抑制剂及其用途 |
| WO2024021957A1 (zh) * | 2022-07-26 | 2024-02-01 | 上海和誉生物医药科技有限公司 | 一种prmt5抑制剂及其制备方法和药学上的应用 |
| WO2024027370A1 (zh) * | 2022-08-03 | 2024-02-08 | 上海和誉生物医药科技有限公司 | 一种含氮三稠环prmt5抑制剂，其制备方法和药学上的用途 |
| WO2024038004A1 (en) | 2022-08-15 | 2024-02-22 | Astrazeneca Ab | Mta-cooperative prmt5 inhibitors for use in the treatment of cancer |
| WO2024037459A1 (zh) * | 2022-08-18 | 2024-02-22 | 南京明德新药研发有限公司 | 含酰胺的杂环衍生物及其应用 |
| CN117658980A (zh) * | 2022-09-08 | 2024-03-08 | 郑州同源康医药有限公司 | 双环类prmt5抑制剂 |
| WO2024067445A1 (zh) * | 2022-09-26 | 2024-04-04 | 上海湃隆生物科技有限公司 | 新型prmt5抑制剂及其应用 |
| CN115677708A (zh) * | 2022-10-19 | 2023-02-03 | 五邑大学 | 一种吡咯并喹喔啉的制备方法 |
| US11845749B1 (en) | 2023-07-13 | 2023-12-19 | King Faisal University | Substituted pyrido[4′,3′:5,6]pyrazino[1,2-a]indoles as anticancer agents |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106573932B (zh) | 2014-08-22 | 2019-07-30 | 默克专利股份公司 | 吲唑类 |
| JP2020530496A (ja) * | 2017-08-09 | 2020-10-22 | プレリュード セラピューティクス，インコーポレイティド | タンパク質アルギニンメチルトランスフェラーゼ５（ｐｒｍｔ５）の選択的阻害剤 |
| US20210277009A1 (en) * | 2018-08-07 | 2021-09-09 | Merck Sharp & Dohme Corp. | Prmt5 inhibitors |
| US20210309687A1 (en) * | 2018-08-07 | 2021-10-07 | Merck Sharp & Dohme Corp. | Prmt5 inhibitors |
| JP2023513580A (ja) * | 2020-02-12 | 2023-03-31 | アムジェン インコーポレイテッド | 新規ｐｒｍｔ５阻害剤 |
-
2021
- 2021-12-15 WO PCT/US2021/063540 patent/WO2022132914A1/en active Application Filing
- 2021-12-15 CN CN202180093453.1A patent/CN116888120A/zh active Pending
- 2021-12-15 US US17/552,016 patent/US11845760B2/en active Active
- 2021-12-15 AU AU2021400942A patent/AU2021400942A1/en active Pending
- 2021-12-15 TW TW110146964A patent/TW202233183A/zh unknown
- 2021-12-15 MX MX2023007192A patent/MX2023007192A/es unknown
- 2021-12-15 EP EP21847813.9A patent/EP4263545A1/en active Pending
- 2021-12-15 JP JP2023535834A patent/JP2023550530A/ja active Pending
- 2021-12-15 CA CA3204823A patent/CA3204823A1/en active Pending
- 2021-12-15 AR ARP210103508A patent/AR124369A1/es unknown
- 2021-12-15 PE PE2023001893A patent/PE20231295A1/es unknown
- 2021-12-15 CR CR20230310A patent/CR20230310A/es unknown
- 2021-12-15 UY UY0001039565A patent/UY39565A/es unknown
- 2021-12-15 IL IL303451A patent/IL303451A/en unknown
- 2021-12-15 KR KR1020237023776A patent/KR20230121820A/ko unknown
-
2023
- 2023-06-14 CL CL2023001738A patent/CL2023001738A1/es unknown
- 2023-06-22 CO CONC2023/0008167A patent/CO2023008167A2/es unknown
- 2023-11-06 US US18/502,780 patent/US20240092794A1/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CL2023001738A1 (es) | 2023-11-17 |
| US20240092794A1 (en) | 2024-03-21 |
| IL303451A (en) | 2023-08-01 |
| CA3204823A1 (en) | 2022-06-23 |
| JP2023550530A (ja) | 2023-12-01 |
| AR124369A1 (es) | 2023-03-22 |
| CN116888120A (zh) | 2023-10-13 |
| CO2023008167A2 (es) | 2023-07-21 |
| UY39565A (es) | 2022-06-30 |
| AU2021400942A1 (en) | 2023-07-06 |
| US11845760B2 (en) | 2023-12-19 |
| CR20230310A (es) | 2023-09-01 |
| EP4263545A1 (en) | 2023-10-25 |
| KR20230121820A (ko) | 2023-08-21 |
| WO2022132914A1 (en) | 2022-06-23 |
| MX2023007192A (es) | 2023-07-03 |
| TW202233183A (zh) | 2022-09-01 |
| US20220194955A1 (en) | 2022-06-23 |
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