JPWO2019155468A5 - - Google Patents
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- JPWO2019155468A5 JPWO2019155468A5 JP2020542875A JP2020542875A JPWO2019155468A5 JP WO2019155468 A5 JPWO2019155468 A5 JP WO2019155468A5 JP 2020542875 A JP2020542875 A JP 2020542875A JP 2020542875 A JP2020542875 A JP 2020542875A JP WO2019155468 A5 JPWO2019155468 A5 JP WO2019155468A5
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- compound according
- aspects
- methyl
- hydrogen
- mixture
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- 150000001875 compounds Chemical class 0.000 description 96
- -1 bicyclo [2.2.1] heptyl Chemical group 0.000 description 80
- 239000000203 mixture Substances 0.000 description 59
- 229910052739 hydrogen Inorganic materials 0.000 description 43
- 239000001257 hydrogen Substances 0.000 description 43
- 125000000623 heterocyclic group Chemical group 0.000 description 36
- 238000000034 method Methods 0.000 description 35
- 125000000217 alkyl group Chemical group 0.000 description 34
- 125000001424 substituent group Chemical group 0.000 description 33
- 125000001072 heteroaryl group Chemical group 0.000 description 28
- 125000003118 aryl group Chemical group 0.000 description 25
- 125000003710 aryl alkyl group Chemical group 0.000 description 23
- 150000002431 hydrogen Chemical class 0.000 description 23
- 150000001345 alkine derivatives Chemical class 0.000 description 21
- 239000008194 pharmaceutical composition Substances 0.000 description 21
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 description 20
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 20
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 20
- 229910052805 deuterium Inorganic materials 0.000 description 20
- 239000000651 prodrug Substances 0.000 description 20
- 229940002612 prodrug Drugs 0.000 description 20
- 150000003839 salts Chemical class 0.000 description 20
- 239000012453 solvate Substances 0.000 description 19
- 239000000126 substance Substances 0.000 description 19
- 150000004677 hydrates Chemical class 0.000 description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 description 12
- 125000004093 cyano group Chemical group *C#N 0.000 description 9
- 125000004419 alkynylene group Chemical group 0.000 description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
- 125000004474 heteroalkylene group Chemical group 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 125000002947 alkylene group Chemical group 0.000 description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 6
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 208000024891 symptom Diseases 0.000 description 5
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 description 4
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 4
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 4
- 125000004450 alkenylene group Chemical group 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 4
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000035475 disorder Diseases 0.000 description 4
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 4
- 102000008122 Casein Kinase I Human genes 0.000 description 3
- 108010049812 Casein Kinase I Proteins 0.000 description 3
- 102000013702 Cyclin-Dependent Kinase 9 Human genes 0.000 description 3
- 108010025461 Cyclin-Dependent Kinase 9 Proteins 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000001404 mediated effect Effects 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 125000003566 oxetanyl group Chemical group 0.000 description 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 3
- 208000030507 AIDS Diseases 0.000 description 2
- 206010009944 Colon cancer Diseases 0.000 description 2
- 241000725303 Human immunodeficiency virus Species 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 208000036142 Viral infection Diseases 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 208000032839 leukemia Diseases 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 239000006186 oral dosage form Substances 0.000 description 2
- 125000005981 pentynyl group Chemical group 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 230000002062 proliferating effect Effects 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- 208000017520 skin disease Diseases 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 230000009385 viral infection Effects 0.000 description 2
- 208000031261 Acute myeloid leukaemia Diseases 0.000 description 1
- 206010005003 Bladder cancer Diseases 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 206010008342 Cervix carcinoma Diseases 0.000 description 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 description 1
- 208000000461 Esophageal Neoplasms Diseases 0.000 description 1
- 208000032612 Glial tumor Diseases 0.000 description 1
- 206010018338 Glioma Diseases 0.000 description 1
- 102000045959 Interleukin-1 Receptor-Like 1 Human genes 0.000 description 1
- 108700003107 Interleukin-1 Receptor-Like 1 Proteins 0.000 description 1
- 208000008839 Kidney Neoplasms Diseases 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 206010025323 Lymphomas Diseases 0.000 description 1
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 description 1
- 206010029260 Neuroblastoma Diseases 0.000 description 1
- 206010030155 Oesophageal carcinoma Diseases 0.000 description 1
- 206010033128 Ovarian cancer Diseases 0.000 description 1
- 206010061535 Ovarian neoplasm Diseases 0.000 description 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 1
- 108091000080 Phosphotransferase Proteins 0.000 description 1
- 208000012641 Pigmentation disease Diseases 0.000 description 1
- 206010035226 Plasma cell myeloma Diseases 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- 206010038389 Renal cancer Diseases 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- 208000000453 Skin Neoplasms Diseases 0.000 description 1
- 206010041067 Small cell lung cancer Diseases 0.000 description 1
- 208000005718 Stomach Neoplasms Diseases 0.000 description 1
- 208000024313 Testicular Neoplasms Diseases 0.000 description 1
- 206010057644 Testis cancer Diseases 0.000 description 1
- 208000024770 Thyroid neoplasm Diseases 0.000 description 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 1
- 208000002495 Uterine Neoplasms Diseases 0.000 description 1
- 208000009956 adenocarcinoma Diseases 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 210000001185 bone marrow Anatomy 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 201000010881 cervical cancer Diseases 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 201000004101 esophageal cancer Diseases 0.000 description 1
- 206010017758 gastric cancer Diseases 0.000 description 1
- 208000005017 glioblastoma Diseases 0.000 description 1
- 201000010536 head and neck cancer Diseases 0.000 description 1
- 208000014829 head and neck neoplasm Diseases 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000006207 intravenous dosage form Substances 0.000 description 1
- 201000010982 kidney cancer Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 201000007270 liver cancer Diseases 0.000 description 1
- 208000014018 liver neoplasm Diseases 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 201000000050 myeloid neoplasm Diseases 0.000 description 1
- 208000002154 non-small cell lung carcinoma Diseases 0.000 description 1
- 201000008968 osteosarcoma Diseases 0.000 description 1
- 201000002528 pancreatic cancer Diseases 0.000 description 1
- 208000008443 pancreatic carcinoma Diseases 0.000 description 1
- 239000006201 parenteral dosage form Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 102000020233 phosphotransferase Human genes 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 201000000849 skin cancer Diseases 0.000 description 1
- 210000004927 skin cell Anatomy 0.000 description 1
- 208000000587 small cell lung carcinoma Diseases 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 206010041823 squamous cell carcinoma Diseases 0.000 description 1
- 201000011549 stomach cancer Diseases 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 201000003120 testicular cancer Diseases 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 201000002510 thyroid cancer Diseases 0.000 description 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 description 1
- 201000005112 urinary bladder cancer Diseases 0.000 description 1
- 206010046766 uterine cancer Diseases 0.000 description 1
- 230000029812 viral genome replication Effects 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201862627908P | 2018-02-08 | 2018-02-08 | |
| US201862627921P | 2018-02-08 | 2018-02-08 | |
| US62/627,908 | 2018-02-08 | ||
| US62/627,921 | 2018-02-08 | ||
| PCT/IL2019/050151 WO2019155468A1 (en) | 2018-02-08 | 2019-02-07 | Heteroaryl compounds, pharmaceutical compositions thereof, and their therapeutic use |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2021512922A JP2021512922A (ja) | 2021-05-20 |
| JPWO2019155468A5 true JPWO2019155468A5 (https=) | 2022-02-17 |
| JP2021512922A5 JP2021512922A5 (https=) | 2022-02-17 |
Family
ID=65635772
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020542875A Pending JP2021512922A (ja) | 2018-02-08 | 2019-02-07 | ヘテロアリール化合物、それらの医薬組成物、及びそれら治療的使用 |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US20200383984A1 (https=) |
| EP (1) | EP3749666A1 (https=) |
| JP (1) | JP2021512922A (https=) |
| KR (1) | KR20200130287A (https=) |
| CN (1) | CN111971280A (https=) |
| AU (1) | AU2019219678A1 (https=) |
| BR (1) | BR112020016064A2 (https=) |
| CA (1) | CA3090063A1 (https=) |
| IL (1) | IL276290A (https=) |
| MX (1) | MX2020008375A (https=) |
| WO (1) | WO2019155468A1 (https=) |
Families Citing this family (7)
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|---|---|---|---|---|
| MX384172B (es) | 2015-08-04 | 2025-03-14 | Yissum Res Dev Co Of Hebrew Univ Jerusalem Ltd | Derivados de pirazol pirimidina y sus usos. |
| IL288547B2 (en) * | 2019-06-03 | 2025-10-01 | Biotheryx Inc | Non-hygroscopic crystalline pyrazole compound salts, pharmaceutical preparations thereof and use thereof |
| US20230047732A1 (en) * | 2020-01-13 | 2023-02-16 | Biotheryx, Inc. | Pyrazolylpyrimidines and use thereof |
| WO2022204220A1 (en) * | 2021-03-24 | 2022-09-29 | Biotheryx, Inc. | Pyrazolylpyrimidines for treating malignant solid tumor |
| US11752151B2 (en) * | 2021-07-12 | 2023-09-12 | Buddhist Tzu Chi Medical Foundation | Method for enhancing hair growth |
| US20230053307A1 (en) * | 2021-07-19 | 2023-02-16 | Buddhist Tzu Chi Medical Foundation | Method for preventing or treating skin disorders and conditions |
| CN119255980A (zh) * | 2022-06-01 | 2025-01-03 | 西姆莱斯股份公司 | 具有环丙基结构的香料 |
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2019
- 2019-02-07 WO PCT/IL2019/050151 patent/WO2019155468A1/en not_active Ceased
- 2019-02-07 MX MX2020008375A patent/MX2020008375A/es unknown
- 2019-02-07 JP JP2020542875A patent/JP2021512922A/ja active Pending
- 2019-02-07 EP EP19708681.2A patent/EP3749666A1/en not_active Withdrawn
- 2019-02-07 AU AU2019219678A patent/AU2019219678A1/en not_active Abandoned
- 2019-02-07 CN CN201980019508.7A patent/CN111971280A/zh active Pending
- 2019-02-07 BR BR112020016064-4A patent/BR112020016064A2/pt not_active IP Right Cessation
- 2019-02-07 CA CA3090063A patent/CA3090063A1/en active Pending
- 2019-02-07 US US16/968,273 patent/US20200383984A1/en not_active Abandoned
- 2019-02-07 KR KR1020207025808A patent/KR20200130287A/ko not_active Ceased
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2020
- 2020-07-26 IL IL276290A patent/IL276290A/en unknown
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2023
- 2023-01-25 US US18/159,176 patent/US12138265B2/en active Active
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