AU2020283505A1 - Heterocyclic compounds as PRMT5 inhibitors - Google Patents
Heterocyclic compounds as PRMT5 inhibitors Download PDFInfo
- Publication number
- AU2020283505A1 AU2020283505A1 AU2020283505A AU2020283505A AU2020283505A1 AU 2020283505 A1 AU2020283505 A1 AU 2020283505A1 AU 2020283505 A AU2020283505 A AU 2020283505A AU 2020283505 A AU2020283505 A AU 2020283505A AU 2020283505 A1 AU2020283505 A1 AU 2020283505A1
- Authority
- AU
- Australia
- Prior art keywords
- optionally substituted
- compound
- pyrrolo
- quinolin
- ethyl
- 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.)
- Abandoned
Links
- 101710084427 Protein arginine N-methyltransferase 5 Proteins 0.000 title claims abstract description 31
- 102100034607 Protein arginine N-methyltransferase 5 Human genes 0.000 title claims abstract description 31
- 239000003112 inhibitor Substances 0.000 title abstract description 7
- 150000002391 heterocyclic compounds Chemical class 0.000 title description 4
- 238000000034 method Methods 0.000 claims abstract description 85
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 27
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 21
- 201000011510 cancer Diseases 0.000 claims abstract description 17
- 208000035473 Communicable disease Diseases 0.000 claims abstract description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 231
- -1 4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl Chemical group 0.000 claims description 156
- VCVOSERVUCJNPR-UHFFFAOYSA-N cyclopentane-1,2-diol Chemical compound OC1CCCC1O VCVOSERVUCJNPR-UHFFFAOYSA-N 0.000 claims description 56
- 125000000217 alkyl group Chemical group 0.000 claims description 51
- 125000001424 substituent group Chemical group 0.000 claims description 38
- 229910052731 fluorine Inorganic materials 0.000 claims description 33
- 229910052801 chlorine Inorganic materials 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 19
- 208000035475 disorder Diseases 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 15
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- 125000000743 hydrocarbylene group Chemical group 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 8
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 8
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
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- YRVLRJRZAIDEJU-NOOVBMIQSA-N N1NCC=2C1=NC1=CC(=CC=C1C=2)CC[C@@H]1[C@H]([C@H]([C@@H](C1)N1C=CC2=C1N=CN=C2)O)O Chemical class N1NCC=2C1=NC1=CC(=CC=C1C=2)CC[C@@H]1[C@H]([C@H]([C@@H](C1)N1C=CC2=C1N=CN=C2)O)O YRVLRJRZAIDEJU-NOOVBMIQSA-N 0.000 claims description 4
- ZVITYBOAZGMLFE-NOOVBMIQSA-N N1OCC=2C1=NC1=CC(=CC=C1C=2)CC[C@@H]1[C@H]([C@H]([C@@H](C1)N1C=CC2=C1N=CN=C2)O)O Chemical class N1OCC=2C1=NC1=CC(=CC=C1C=2)CC[C@@H]1[C@H]([C@H]([C@@H](C1)N1C=CC2=C1N=CN=C2)O)O ZVITYBOAZGMLFE-NOOVBMIQSA-N 0.000 claims description 4
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- FKFCLBYITBFCNF-NOOVBMIQSA-N N=1C=CN2C=NC=3C=C(C=CC=3C2=1)CC[C@@H]1[C@H]([C@H]([C@@H](C1)N1C=CC2=C1N=CN=C2)O)O Chemical class N=1C=CN2C=NC=3C=C(C=CC=3C2=1)CC[C@@H]1[C@H]([C@H]([C@@H](C1)N1C=CC2=C1N=CN=C2)O)O FKFCLBYITBFCNF-NOOVBMIQSA-N 0.000 claims description 4
- FCLAPPNPMKAIRP-NOOVBMIQSA-N N=1CCN2C=NC=3C=C(C=CC=3C2=1)CC[C@@H]1[C@H]([C@H]([C@@H](C1)N1C=CC2=C1N=CN=C2)O)O Chemical class N=1CCN2C=NC=3C=C(C=CC=3C2=1)CC[C@@H]1[C@H]([C@H]([C@@H](C1)N1C=CC2=C1N=CN=C2)O)O FCLAPPNPMKAIRP-NOOVBMIQSA-N 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- JTZAMAGQUVDCAS-GECPAALWSA-N N1=CN=CC2=C1N(C=C2)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)CCC=1C=CC=2C(=NC=3NCCCC=3C=2)C=1 Chemical class N1=CN=CC2=C1N(C=C2)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)CCC=1C=CC=2C(=NC=3NCCCC=3C=2)C=1 JTZAMAGQUVDCAS-GECPAALWSA-N 0.000 claims description 3
- MZJTZFSKAMUKMJ-JPAWQOSXSA-N N=1C=CN2C=NC=3C=C(C=CC=3C2=1)CC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)N1C=CC2=C1N=CN=C2 Chemical class N=1C=CN2C=NC=3C=C(C=CC=3C2=1)CC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)N1C=CC2=C1N=CN=C2 MZJTZFSKAMUKMJ-JPAWQOSXSA-N 0.000 claims description 3
- TVZPCTRFMXFNPF-JPAWQOSXSA-N N=1CCN2C=NC=3C=C(C=CC=3C2=1)CC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)N1C=CC2=C1N=CN=C2 Chemical class N=1CCN2C=NC=3C=C(C=CC=3C2=1)CC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)N1C=CC2=C1N=CN=C2 TVZPCTRFMXFNPF-JPAWQOSXSA-N 0.000 claims description 3
- HSXABXZICZHUFH-UHFFFAOYSA-N 1,2,3,4-tetrahydrobenzo[b][1,8]naphthyridin-3-ol Chemical class N1CC(CC=2C=C3C(=NC1=2)C=CC=C3)O HSXABXZICZHUFH-UHFFFAOYSA-N 0.000 claims description 2
- ZCTBSFQMEZPPFF-JTQLQIEISA-N N1[C@@H](CC=2C1=NC1=CC=CC=C1C=2)CO Chemical class N1[C@@H](CC=2C1=NC1=CC=CC=C1C=2)CO ZCTBSFQMEZPPFF-JTQLQIEISA-N 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 142
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 126
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 110
- 239000000203 mixture Substances 0.000 description 105
- 239000000243 solution Substances 0.000 description 92
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
- 229910001868 water Inorganic materials 0.000 description 66
- 239000000543 intermediate Substances 0.000 description 63
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 56
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 55
- 238000001914 filtration Methods 0.000 description 54
- 235000019439 ethyl acetate Nutrition 0.000 description 53
- 239000000706 filtrate Substances 0.000 description 51
- 239000012267 brine Substances 0.000 description 49
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 49
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
- 238000010898 silica gel chromatography Methods 0.000 description 39
- 239000011734 sodium Substances 0.000 description 39
- 238000003786 synthesis reaction Methods 0.000 description 35
- 239000012044 organic layer Substances 0.000 description 34
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- 230000015572 biosynthetic process Effects 0.000 description 30
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 28
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 26
- 239000012300 argon atmosphere Substances 0.000 description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
- 239000003208 petroleum Substances 0.000 description 19
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- 238000006243 chemical reaction Methods 0.000 description 18
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- 239000000284 extract Substances 0.000 description 15
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- 229910002027 silica gel Inorganic materials 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 14
- 125000004093 cyano group Chemical group *C#N 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- 125000003342 alkenyl group Chemical group 0.000 description 13
- 125000000304 alkynyl group Chemical group 0.000 description 13
- 125000000753 cycloalkyl group Chemical group 0.000 description 12
- 229920006395 saturated elastomer Polymers 0.000 description 12
- 238000004587 chromatography analysis Methods 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- 238000000746 purification Methods 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
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- DHYHYLGCQVVLOQ-UHFFFAOYSA-N 3-bromoaniline Chemical compound NC1=CC=CC(Br)=C1 DHYHYLGCQVVLOQ-UHFFFAOYSA-N 0.000 description 8
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 7
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- 125000003545 alkoxy group Chemical group 0.000 description 7
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- 238000005481 NMR spectroscopy Methods 0.000 description 6
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- MZSAMHOCTRNOIZ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylaniline Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(NC2=CC=CC=C2)C=CC=1 MZSAMHOCTRNOIZ-UHFFFAOYSA-N 0.000 description 5
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 4
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- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 201000011549 stomach cancer Diseases 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
- 239000012414 tert-butyl nitrite Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000037426 transcriptional repression Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 125000005423 trihalomethanesulfonamido group Chemical group 0.000 description 1
- 125000005152 trihalomethanesulfonyl group Chemical group 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000001086 yeast two-hybrid system Methods 0.000 description 1
Classifications
-
- 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
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- 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
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- 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
- C07H19/14—Pyrrolo-pyrimidine radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201962854435P | 2019-05-30 | 2019-05-30 | |
| US62/854,435 | 2019-05-30 | ||
| US202062966337P | 2020-01-27 | 2020-01-27 | |
| US62/966,337 | 2020-01-27 | ||
| PCT/US2020/034711 WO2020243178A1 (fr) | 2019-05-30 | 2020-05-27 | Composés hétérocycliques en tant qu'inhibiteurs de prmt5 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2020283505A1 true AU2020283505A1 (en) | 2021-12-23 |
Family
ID=73553050
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2020283505A Abandoned AU2020283505A1 (en) | 2019-05-30 | 2020-05-27 | Heterocyclic compounds as PRMT5 inhibitors |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP3976038A4 (fr) |
| JP (1) | JP2022534998A (fr) |
| KR (1) | KR20220016194A (fr) |
| CN (1) | CN114126614A (fr) |
| AU (1) | AU2020283505A1 (fr) |
| CA (1) | CA3141855A1 (fr) |
| WO (1) | WO2020243178A1 (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2024032572A1 (fr) * | 2022-08-09 | 2024-02-15 | 上海湃隆生物科技有限公司 | Nouvel inhibiteur de prmt5 et son utilisation |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI791251B (zh) * | 2015-08-26 | 2023-02-01 | 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 |
| CA2969295A1 (fr) * | 2016-06-06 | 2017-12-06 | Pfizer Inc. | Derives de carbonucleosides substitues et leur utilisation comme inhibiteur de prmt5 |
| WO2018065365A1 (fr) * | 2016-10-03 | 2018-04-12 | Janssen Pharmaceutica Nv | Nouveaux analogues de carbanucléoside substitués par un système cyclique, monocyclique et bicyclique destinés à être utilisés en tant qu'inhibiteurs de prmt5 |
| WO2018152548A1 (fr) * | 2017-02-20 | 2018-08-23 | Prelude Therapeutics, Incorporated | Inhibiteurs sélectifs de la protéine arginine méthyltransférase 5 (prmt5) |
| PL3665179T3 (pl) * | 2017-08-09 | 2021-11-29 | Prelude Therapeutics, Incorporated | Selektywne inhibitory metylotransferazy argininowej białek 5 (prmt5) |
| AU2018381004B2 (en) * | 2017-12-05 | 2021-04-29 | Angex Pharmaceutical, Inc. | Heterocyclic compounds as PRMT5 inhibitors |
| RS63623B1 (sr) * | 2017-12-13 | 2022-10-31 | Lupin Ltd | Supstituisana biciklična heterociklična jedinjenja kao inhibitori prmt5 |
| CA3108388A1 (fr) * | 2018-08-07 | 2020-02-13 | Merck Sharp & Dohme Corp. | Inhibiteurs de prmt5 |
-
2020
- 2020-05-27 AU AU2020283505A patent/AU2020283505A1/en not_active Abandoned
- 2020-05-27 CA CA3141855A patent/CA3141855A1/fr active Pending
- 2020-05-27 EP EP20814821.3A patent/EP3976038A4/fr not_active Withdrawn
- 2020-05-27 KR KR1020217043087A patent/KR20220016194A/ko not_active Application Discontinuation
- 2020-05-27 WO PCT/US2020/034711 patent/WO2020243178A1/fr unknown
- 2020-05-27 JP JP2021570954A patent/JP2022534998A/ja active Pending
- 2020-05-27 CN CN202080052198.1A patent/CN114126614A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP3976038A1 (fr) | 2022-04-06 |
| WO2020243178A1 (fr) | 2020-12-03 |
| JP2022534998A (ja) | 2022-08-04 |
| CA3141855A1 (fr) | 2020-12-03 |
| CN114126614A (zh) | 2022-03-01 |
| EP3976038A4 (fr) | 2023-07-12 |
| KR20220016194A (ko) | 2022-02-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK5 | Application lapsed section 142(2)(e) - patent request and compl. specification not accepted |