JP2024088768A5 - - Google Patents
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- JP2024088768A5 JP2024088768A5 JP2024063204A JP2024063204A JP2024088768A5 JP 2024088768 A5 JP2024088768 A5 JP 2024088768A5 JP 2024063204 A JP2024063204 A JP 2024063204A JP 2024063204 A JP2024063204 A JP 2024063204A JP 2024088768 A5 JP2024088768 A5 JP 2024088768A5
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- JP
- Japan
- Prior art keywords
- compound
- cancer
- inhibitors
- alkyl
- gpr55
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims 12
- 238000000034 method Methods 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 102100033061 G-protein coupled receptor 55 Human genes 0.000 claims 4
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- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims 2
- 239000004471 Glycine Substances 0.000 claims 2
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- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 2
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims 2
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- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 2
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- 235000004279 alanine Nutrition 0.000 claims 2
- 125000000539 amino acid group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 235000003704 aspartic acid Nutrition 0.000 claims 2
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 2
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- 235000013922 glutamic acid Nutrition 0.000 claims 2
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- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims 2
- 229960000310 isoleucine Drugs 0.000 claims 2
- 229930182817 methionine Natural products 0.000 claims 2
- 235000006109 methionine Nutrition 0.000 claims 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 2
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims 1
- 239000004475 Arginine Substances 0.000 claims 1
- 208000020084 Bone disease Diseases 0.000 claims 1
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- 108010025464 Cyclin-Dependent Kinase 4 Proteins 0.000 claims 1
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- 102000037984 Inhibitory immune checkpoint proteins Human genes 0.000 claims 1
- 108091008026 Inhibitory immune checkpoint proteins Proteins 0.000 claims 1
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims 1
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims 1
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- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
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- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
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- 102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 claims 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
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- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 claims 1
- 239000004037 angiogenesis inhibitor Substances 0.000 claims 1
- 229940121369 angiogenesis inhibitor Drugs 0.000 claims 1
- 230000000340 anti-metabolite Effects 0.000 claims 1
- 229940100197 antimetabolite Drugs 0.000 claims 1
- 239000002256 antimetabolite Substances 0.000 claims 1
- 229940034982 antineoplastic agent Drugs 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims 1
- 239000003886 aromatase inhibitor Substances 0.000 claims 1
- 229940046844 aromatase inhibitors Drugs 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 208000006990 cholangiocarcinoma Diseases 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 208000010643 digestive system disease Diseases 0.000 claims 1
- 229940121647 egfr inhibitor Drugs 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 208000018685 gastrointestinal system disease Diseases 0.000 claims 1
- 229960005277 gemcitabine Drugs 0.000 claims 1
- SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 claims 1
- 208000005017 glioblastoma Diseases 0.000 claims 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 239000012274 immune-checkpoint protein inhibitor Substances 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 229940124302 mTOR inhibitor Drugs 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 239000003628 mammalian target of rapamycin inhibitor Substances 0.000 claims 1
- 230000000394 mitotic effect Effects 0.000 claims 1
- 208000004296 neuralgia Diseases 0.000 claims 1
- 208000021722 neuropathic pain Diseases 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims 1
- 230000026731 phosphorylation Effects 0.000 claims 1
- 238000006366 phosphorylation reaction Methods 0.000 claims 1
- 229910052697 platinum Inorganic materials 0.000 claims 1
- 206010041823 squamous cell carcinoma Diseases 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 208000022679 triple-negative breast carcinoma Diseases 0.000 claims 1
- 210000004881 tumor cell Anatomy 0.000 claims 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims 1
- 239000004474 valine Substances 0.000 claims 1
- 210000005166 vasculature Anatomy 0.000 claims 1
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201962906228P | 2019-09-26 | 2019-09-26 | |
| US62/906,228 | 2019-09-26 | ||
| PCT/US2020/052829 WO2021062231A2 (en) | 2019-09-26 | 2020-09-25 | Cannabinoid prodrug compounds |
| JP2022519475A JP7475731B2 (ja) | 2019-09-26 | 2020-09-25 | カンナビノイドプロドラッグ化合物 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022519475A Division JP7475731B2 (ja) | 2019-09-26 | 2020-09-25 | カンナビノイドプロドラッグ化合物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2024088768A JP2024088768A (ja) | 2024-07-02 |
| JP2024088768A5 true JP2024088768A5 (enExample) | 2024-10-28 |
Family
ID=75166839
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022519475A Active JP7475731B2 (ja) | 2019-09-26 | 2020-09-25 | カンナビノイドプロドラッグ化合物 |
| JP2024063204A Pending JP2024088768A (ja) | 2019-09-26 | 2024-04-10 | カンナビノイドプロドラッグ化合物 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022519475A Active JP7475731B2 (ja) | 2019-09-26 | 2020-09-25 | カンナビノイドプロドラッグ化合物 |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US11980602B2 (enExample) |
| EP (1) | EP4034100A4 (enExample) |
| JP (2) | JP7475731B2 (enExample) |
| CA (1) | CA3152168A1 (enExample) |
| WO (1) | WO2021062231A2 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116234812A (zh) * | 2020-11-25 | 2023-06-06 | 成都百裕制药股份有限公司 | 大麻素类化合物的制备方法 |
| CN115315418B (zh) * | 2021-04-06 | 2023-03-21 | 山东绿叶制药有限公司 | 大麻二酚前药及其药物组合物和应用 |
| CN116253671B (zh) * | 2021-12-10 | 2025-07-04 | 德义制药有限公司 | 一种大麻二酚衍生物及其制备方法和应用 |
| AU2023280314A1 (en) * | 2022-05-31 | 2024-12-12 | Trait Biosciences, Inc. | Water-soluble cannabinoid prodrugs compositions and methods of synthesizing the same |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008107879A1 (en) * | 2007-03-05 | 2008-09-12 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Novel cannabidiol derivatives and their use as anti-inflammatory agents |
| CA2694325C (en) | 2007-07-30 | 2015-09-22 | Alltranz Inc. | Prodrugs of cannabidiol, compositions comprising prodrugs of cannabidiol and methods of using the same |
| KR102202133B1 (ko) * | 2016-01-29 | 2021-01-14 | 더 유니버시티 오브 미시시피 | 생물학적으로 활성인 칸나비디올 유사체 |
| CN109311838A (zh) * | 2016-04-15 | 2019-02-05 | 蒂温诺特技术有限公司 | 大麻素前药的生物合成 |
| AU2017361791A1 (en) * | 2016-11-15 | 2019-06-13 | Teewinot Technologies Limited | Bio-stable cannabinoid compounds and methods for enhancing their physiological concentration |
| CN118348657A (zh) | 2019-06-06 | 2024-07-16 | 应用材料公司 | 生成复合影像的成像系统及方法 |
-
2020
- 2020-09-25 CA CA3152168A patent/CA3152168A1/en active Pending
- 2020-09-25 JP JP2022519475A patent/JP7475731B2/ja active Active
- 2020-09-25 WO PCT/US2020/052829 patent/WO2021062231A2/en not_active Ceased
- 2020-09-25 EP EP20867541.3A patent/EP4034100A4/en active Pending
-
2022
- 2022-03-24 US US17/703,068 patent/US11980602B2/en active Active
-
2024
- 2024-04-10 JP JP2024063204A patent/JP2024088768A/ja active Pending
- 2024-05-13 US US18/662,582 patent/US20240408046A1/en not_active Abandoned
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