AU2020336975A1 - Perk inhibiting pyrrolopyrimidine compounds - Google Patents
Perk inhibiting pyrrolopyrimidine compounds Download PDFInfo
- Publication number
- AU2020336975A1 AU2020336975A1 AU2020336975A AU2020336975A AU2020336975A1 AU 2020336975 A1 AU2020336975 A1 AU 2020336975A1 AU 2020336975 A AU2020336975 A AU 2020336975A AU 2020336975 A AU2020336975 A AU 2020336975A AU 2020336975 A1 AU2020336975 A1 AU 2020336975A1
- Authority
- AU
- Australia
- Prior art keywords
- amino
- pyrrolo
- pyrimidin
- alkyl
- methyl
- 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
- 230000002401 inhibitory effect Effects 0.000 title abstract description 8
- 150000004944 pyrrolopyrimidines Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 198
- 238000000034 method Methods 0.000 claims abstract description 84
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 11
- 201000010099 disease Diseases 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 119
- 125000005843 halogen group Chemical group 0.000 claims description 98
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 92
- 229910052805 deuterium Inorganic materials 0.000 claims description 92
- 125000001424 substituent group Chemical group 0.000 claims description 70
- -1 methoxy, ethoxy, propoxy, isopropoxy Chemical group 0.000 claims description 50
- 150000003839 salts Chemical class 0.000 claims description 49
- 206010028980 Neoplasm Diseases 0.000 claims description 42
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
- 201000011510 cancer Diseases 0.000 claims description 32
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 28
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 238000011282 treatment Methods 0.000 claims description 14
- 239000003937 drug carrier Substances 0.000 claims description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- WCYWZMWISLQXQU-FIBGUPNXSA-N trideuteriomethane Chemical compound [2H][C]([2H])[2H] WCYWZMWISLQXQU-FIBGUPNXSA-N 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 7
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
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- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 208000013818 thyroid gland medullary carcinoma Diseases 0.000 description 1
- 208000030045 thyroid gland papillary carcinoma Diseases 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 229940034610 toothpaste Drugs 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 230000002103 transcriptional effect Effects 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- 108091005703 transmembrane proteins Proteins 0.000 description 1
- 102000035160 transmembrane proteins Human genes 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
- 230000004565 tumor cell growth Effects 0.000 description 1
- 230000005748 tumor development Effects 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 231100000588 tumorigenic Toxicity 0.000 description 1
- 230000000381 tumorigenic effect Effects 0.000 description 1
- MEYZYGMYMLNUHJ-UHFFFAOYSA-N tunicamycin Natural products CC(C)CCCCCCCCCC=CC(=O)NC1C(O)C(O)C(CC(O)C2OC(C(O)C2O)N3C=CC(=O)NC3=O)OC1OC4OC(CO)C(O)C(O)C4NC(=O)C MEYZYGMYMLNUHJ-UHFFFAOYSA-N 0.000 description 1
- 230000034512 ubiquitination Effects 0.000 description 1
- 238000010798 ubiquitination Methods 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201962893528P | 2019-08-29 | 2019-08-29 | |
| US62/893,528 | 2019-08-29 | ||
| PCT/US2020/048621 WO2021041975A1 (en) | 2019-08-29 | 2020-08-28 | Perk inhibiting pyrrolopyrimidine compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2020336975A1 true AU2020336975A1 (en) | 2022-03-31 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2020336975A Abandoned AU2020336975A1 (en) | 2019-08-29 | 2020-08-28 | Perk inhibiting pyrrolopyrimidine compounds |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US20220356186A1 (https=) |
| EP (1) | EP4021908A1 (https=) |
| JP (1) | JP2022546414A (https=) |
| KR (1) | KR20220066290A (https=) |
| CN (1) | CN114710956A (https=) |
| AU (1) | AU2020336975A1 (https=) |
| BR (1) | BR112022003584A2 (https=) |
| CA (1) | CA3152508A1 (https=) |
| IL (1) | IL290889A (https=) |
| MX (1) | MX2022002446A (https=) |
| PH (1) | PH12022550491A1 (https=) |
| WO (1) | WO2021041975A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114585606A (zh) | 2019-08-29 | 2022-06-03 | 希伯塞尔股份有限公司 | 抑制perk的化合物 |
| RS65962B1 (sr) | 2020-05-08 | 2024-10-31 | Halia Therapeutics Inc | Inhibitori nek7 kinaze |
| CN117597346A (zh) * | 2021-04-05 | 2024-02-23 | 哈利亚治疗公司 | Nek7抑制剂 |
| WO2022216680A1 (en) * | 2021-04-05 | 2022-10-13 | Halia Therapeutics, Inc. | Nek7 inhibitors |
| US20240287081A1 (en) * | 2021-06-09 | 2024-08-29 | Icahn School Of Medicine At Mount Sinai | Perfluoroalkane substituted pyrazolo[3,4-d]pyrimidin and pyrrolo[2,3-d]pyrimidin compounds and uses thereof |
| US20250000859A1 (en) | 2021-08-25 | 2025-01-02 | Alesta Therapeutics BV | Use of gcn2 inhibitors in treating cancer |
| GB202407386D0 (en) | 2024-05-24 | 2024-07-10 | Apollo Ap45 Ltd | 1H-pyrazolo(4,3-D)pyrimidine derivatives |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3903297A (en) | 1973-11-01 | 1975-09-02 | Upjohn Co | Method of treatment and prophylaxis of gastric hypersecretion and gastric and duodenal ulcers using prostaglandin analogs |
| US7863444B2 (en) * | 1997-03-19 | 2011-01-04 | Abbott Laboratories | 4-aminopyrrolopyrimidines as kinase inhibitors |
| TR199902301T2 (xx) * | 1997-03-19 | 1999-12-21 | Basf Aktiengesellschaft | Pirilo $2,3D]pirimidinler ve onlar�n kullan�m�. |
| CA2794153C (en) | 2010-03-25 | 2018-01-02 | Glaxosmithkline Llc | Substituted indoline derivatives as perk inhibitors |
| JP6493218B2 (ja) * | 2013-11-08 | 2019-04-03 | 小野薬品工業株式会社 | ピロロピリミジン誘導体 |
| WO2016004254A1 (en) | 2014-07-01 | 2016-01-07 | The Regents Of The University Of California | Combined modulation of ire1 |
| WO2016085160A2 (ko) * | 2014-11-28 | 2016-06-02 | (주)네오팜 | 발모촉진용 또는 탈모방지용 조성물 |
| GB201508747D0 (en) * | 2015-05-21 | 2015-07-01 | Univ Edinburgh | Compounds |
| WO2017046739A1 (en) * | 2015-09-15 | 2017-03-23 | Glaxosmithkline Intellectual Property (No.2) Limited | Imidazolidinone derivatives as inhibitors of perk |
| TW201722957A (zh) * | 2015-09-15 | 2017-07-01 | 葛蘭素史克智慧財產（第二）有限公司 | 化學化合物 |
| ES2965081T3 (es) * | 2016-07-07 | 2024-04-11 | Daewoong Pharmaceutical Co Ltd | Derivados 4-aminopirazolo[3,4-d]pirimidinil-azabiciclo y composición farmacéutica que comprende dichos derivados |
| RS65914B1 (sr) * | 2017-04-18 | 2024-10-31 | Lilly Co Eli | Fenil-2-hidroksi-acetilamino-2-metil-fenil jedinjenja |
-
2020
- 2020-08-28 CA CA3152508A patent/CA3152508A1/en active Pending
- 2020-08-28 BR BR112022003584A patent/BR112022003584A2/pt not_active IP Right Cessation
- 2020-08-28 WO PCT/US2020/048621 patent/WO2021041975A1/en not_active Ceased
- 2020-08-28 JP JP2022513164A patent/JP2022546414A/ja active Pending
- 2020-08-28 MX MX2022002446A patent/MX2022002446A/es unknown
- 2020-08-28 KR KR1020227010197A patent/KR20220066290A/ko not_active Ceased
- 2020-08-28 EP EP20771405.6A patent/EP4021908A1/en not_active Withdrawn
- 2020-08-28 CN CN202080073530.2A patent/CN114710956A/zh active Pending
- 2020-08-28 US US17/639,279 patent/US20220356186A1/en active Pending
- 2020-08-28 AU AU2020336975A patent/AU2020336975A1/en not_active Abandoned
- 2020-08-28 PH PH1/2022/550491A patent/PH12022550491A1/en unknown
-
2022
- 2022-02-24 IL IL290889A patent/IL290889A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US20220356186A1 (en) | 2022-11-10 |
| IL290889A (en) | 2022-04-01 |
| CN114710956A (zh) | 2022-07-05 |
| KR20220066290A (ko) | 2022-05-24 |
| PH12022550491A1 (en) | 2023-02-06 |
| EP4021908A1 (en) | 2022-07-06 |
| BR112022003584A2 (pt) | 2022-05-24 |
| MX2022002446A (es) | 2022-06-02 |
| JP2022546414A (ja) | 2022-11-04 |
| WO2021041975A1 (en) | 2021-03-04 |
| CA3152508A1 (en) | 2021-03-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK1 | Application lapsed section 142(2)(a) - no request for examination in relevant period |