JP2019534861A5 - - Google Patents
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- JP2019534861A5 JP2019534861A5 JP2019514780A JP2019514780A JP2019534861A5 JP 2019534861 A5 JP2019534861 A5 JP 2019534861A5 JP 2019514780 A JP2019514780 A JP 2019514780A JP 2019514780 A JP2019514780 A JP 2019514780A JP 2019534861 A5 JP2019534861 A5 JP 2019534861A5
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- JP
- Japan
- Prior art keywords
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- pharmaceutically acceptable
- acceptable salt
- alkyl
- compound according
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 61
- 150000003839 salts Chemical class 0.000 claims description 50
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 150000002367 halogens Chemical class 0.000 claims description 26
- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- -1 methoxypropyl Chemical group 0.000 claims description 18
- 201000010099 disease Diseases 0.000 claims description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 12
- 229940124597 therapeutic agent Drugs 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 10
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 7
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 6
- 208000014644 Brain disease Diseases 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- 206010003246 arthritis Diseases 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 201000011510 cancer Diseases 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 208000019423 liver disease Diseases 0.000 claims description 4
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims description 3
- 208000024827 Alzheimer disease Diseases 0.000 claims description 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 3
- 208000005107 Premature Birth Diseases 0.000 claims description 3
- 208000017442 Retinal disease Diseases 0.000 claims description 3
- 206010012601 diabetes mellitus Diseases 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 201000008482 osteoarthritis Diseases 0.000 claims description 3
- 208000028169 periodontal disease Diseases 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000006712 (C1-C4) deuteroalkyl group Chemical group 0.000 claims description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
- 102000013918 Apolipoproteins E Human genes 0.000 claims description 2
- 108010025628 Apolipoproteins E Proteins 0.000 claims description 2
- 206010003805 Autism Diseases 0.000 claims description 2
- 208000020706 Autistic disease Diseases 0.000 claims description 2
- 208000004051 Chronic Traumatic Encephalopathy Diseases 0.000 claims description 2
- 208000020401 Depressive disease Diseases 0.000 claims description 2
- 201000010374 Down Syndrome Diseases 0.000 claims description 2
- 201000011240 Frontotemporal dementia Diseases 0.000 claims description 2
- 208000010412 Glaucoma Diseases 0.000 claims description 2
- 208000023105 Huntington disease Diseases 0.000 claims description 2
- 208000004575 Infectious Arthritis Diseases 0.000 claims description 2
- 208000001089 Multiple system atrophy Diseases 0.000 claims description 2
- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 claims description 2
- 208000018737 Parkinson disease Diseases 0.000 claims description 2
- 206010035664 Pneumonia Diseases 0.000 claims description 2
- 206010036590 Premature baby Diseases 0.000 claims description 2
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims description 2
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims description 2
- 208000034189 Sclerosis Diseases 0.000 claims description 2
- 208000006011 Stroke Diseases 0.000 claims description 2
- 206010044688 Trisomy 21 Diseases 0.000 claims description 2
- 239000012190 activator Substances 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims description 2
- 125000006242 amine protecting group Chemical group 0.000 claims description 2
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 2
- 230000008499 blood brain barrier function Effects 0.000 claims description 2
- 210000001218 blood-brain barrier Anatomy 0.000 claims description 2
- 208000026106 cerebrovascular disease Diseases 0.000 claims description 2
- 208000010877 cognitive disease Diseases 0.000 claims description 2
- 230000000295 complement effect Effects 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 208000017004 dementia pugilistica Diseases 0.000 claims description 2
- 206010015037 epilepsy Diseases 0.000 claims description 2
- 201000006517 essential tremor Diseases 0.000 claims description 2
- 208000015181 infectious disease Diseases 0.000 claims description 2
- 208000017169 kidney disease Diseases 0.000 claims description 2
- 206010027175 memory impairment Diseases 0.000 claims description 2
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 2
- 230000002025 microglial effect Effects 0.000 claims description 2
- 208000027061 mild cognitive impairment Diseases 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 201000002212 progressive supranuclear palsy Diseases 0.000 claims description 2
- 238000010791 quenching Methods 0.000 claims description 2
- 230000000171 quenching effect Effects 0.000 claims description 2
- 201000000980 schizophrenia Diseases 0.000 claims description 2
- 201000001223 septic arthritis Diseases 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims 2
- 229940122601 Esterase inhibitor Drugs 0.000 claims 1
- 241000282326 Felis catus Species 0.000 claims 1
- 230000006931 brain damage Effects 0.000 claims 1
- 231100000874 brain damage Toxicity 0.000 claims 1
- 208000029028 brain injury Diseases 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims 1
- 229960001231 choline Drugs 0.000 claims 1
- 239000002329 esterase inhibitor Substances 0.000 claims 1
- 201000010901 lateral sclerosis Diseases 0.000 claims 1
- 208000005264 motor neuron disease Diseases 0.000 claims 1
- 210000003205 muscle Anatomy 0.000 claims 1
- 229940076279 serotonin Drugs 0.000 claims 1
- 238000000034 method Methods 0.000 description 27
- 0 CC(NC(*)(C*C(*)(CN(*)*)C=C)C(*)=O)=O Chemical compound CC(NC(*)(C*C(*)(CN(*)*)C=C)C(*)=O)=O 0.000 description 3
- 239000012472 biological sample Substances 0.000 description 3
- 150000002366 halogen compounds Chemical class 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 208000003445 Mouth Neoplasms Diseases 0.000 description 1
- DOHXJAQSKHNDLH-INIZCTEOSA-N NCCCC[C@@H](C(COc(c(F)ccc1)c1F)=O)NC(C1CCCC1)=O Chemical compound NCCCC[C@@H](C(COc(c(F)ccc1)c1F)=O)NC(C1CCCC1)=O DOHXJAQSKHNDLH-INIZCTEOSA-N 0.000 description 1
- OLIMBXKACVCIMM-HNNXBMFYSA-N NCCCC[C@@H](C(COc(c(F)ccc1F)c1F)=O)NC(C1CCCC1)=O Chemical compound NCCCC[C@@H](C(COc(c(F)ccc1F)c1F)=O)NC(C1CCCC1)=O OLIMBXKACVCIMM-HNNXBMFYSA-N 0.000 description 1
- NBIIDGAHKKJKHI-HNNXBMFYSA-N NCCCC[C@@H](C(COc(cc(cc1F)F)c1F)=O)NC(C1CCCC1)=O Chemical compound NCCCC[C@@H](C(COc(cc(cc1F)F)c1F)=O)NC(C1CCCC1)=O NBIIDGAHKKJKHI-HNNXBMFYSA-N 0.000 description 1
- CJMLKFUQJAPXLR-INIZCTEOSA-N NCCCC[C@@H](C(COc(cccc1)c1F)=O)NC(C1CCCC1)=O Chemical compound NCCCC[C@@H](C(COc(cccc1)c1F)=O)NC(C1CCCC1)=O CJMLKFUQJAPXLR-INIZCTEOSA-N 0.000 description 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 1
- 206010064930 age-related macular degeneration Diseases 0.000 description 1
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 208000005017 glioblastoma Diseases 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 208000012987 lip and oral cavity carcinoma Diseases 0.000 description 1
- 208000002780 macular degeneration Diseases 0.000 description 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 1
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 description 1
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 description 1
- 201000002528 pancreatic cancer Diseases 0.000 description 1
- 208000008443 pancreatic carcinoma Diseases 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 230000002207 retinal effect Effects 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662395938P | 2016-09-16 | 2016-09-16 | |
| US62/395,938 | 2016-09-16 | ||
| US201762459456P | 2017-02-15 | 2017-02-15 | |
| US62/459,456 | 2017-02-15 | ||
| PCT/US2017/051912 WO2018053353A1 (en) | 2016-09-16 | 2017-09-15 | Ketone inhibitors of lysine gingipain |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019534861A JP2019534861A (ja) | 2019-12-05 |
| JP2019534861A5 true JP2019534861A5 (https=) | 2020-11-05 |
| JP7113815B2 JP7113815B2 (ja) | 2022-08-05 |
Family
ID=61618978
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019514780A Active JP7113815B2 (ja) | 2016-09-16 | 2017-09-15 | リシンジンジパインのケトン阻害剤 |
Country Status (18)
| Country | Link |
|---|---|
| US (4) | US10730826B2 (https=) |
| EP (2) | EP4480541A3 (https=) |
| JP (1) | JP7113815B2 (https=) |
| KR (1) | KR102780603B1 (https=) |
| CN (1) | CN109983012B (https=) |
| AU (2) | AU2017326466B2 (https=) |
| CA (1) | CA3036862A1 (https=) |
| CL (1) | CL2019000687A1 (https=) |
| CO (1) | CO2019002950A2 (https=) |
| DK (1) | DK3512846T3 (https=) |
| ES (1) | ES2992410T3 (https=) |
| IL (1) | IL265389A (https=) |
| MX (1) | MX2019003087A (https=) |
| PE (1) | PE20190473A1 (https=) |
| PH (1) | PH12019500570A1 (https=) |
| RU (1) | RU2019111188A (https=) |
| TW (1) | TWI787202B (https=) |
| WO (1) | WO2018053353A1 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US12318377B2 (en) | 2013-12-20 | 2025-06-03 | Seed Health, Inc. | Method and system for reducing the likelihood of a porphyromonas gingivalis infection in a human being |
| CN109983012B (zh) | 2016-09-16 | 2023-12-01 | 莱特豪斯制药公司 | 赖氨酸牙龈蛋白酶的酮抑制剂 |
| CN110944637A (zh) | 2017-05-10 | 2020-03-31 | 库特克希米公司 | 氨基吡啶化合物及其制备方法和使用方法 |
| BR112021011970A2 (pt) * | 2018-12-20 | 2021-09-08 | Takeda Pharmaceutical Company Limited | Derivados de ilídeo sulfoxônio como sondas para cisteína-proteases |
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| CN110944637A (zh) | 2017-05-10 | 2020-03-31 | 库特克希米公司 | 氨基吡啶化合物及其制备方法和使用方法 |
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2017
- 2017-09-15 CN CN201780068518.0A patent/CN109983012B/zh active Active
- 2017-09-15 AU AU2017326466A patent/AU2017326466B2/en active Active
- 2017-09-15 RU RU2019111188A patent/RU2019111188A/ru unknown
- 2017-09-15 ES ES17851664T patent/ES2992410T3/es active Active
- 2017-09-15 CA CA3036862A patent/CA3036862A1/en active Pending
- 2017-09-15 DK DK17851664.7T patent/DK3512846T3/da active
- 2017-09-15 KR KR1020197010797A patent/KR102780603B1/ko active Active
- 2017-09-15 TW TW106131764A patent/TWI787202B/zh active
- 2017-09-15 JP JP2019514780A patent/JP7113815B2/ja active Active
- 2017-09-15 PE PE2019000533A patent/PE20190473A1/es unknown
- 2017-09-15 MX MX2019003087A patent/MX2019003087A/es unknown
- 2017-09-15 EP EP24187049.2A patent/EP4480541A3/en active Pending
- 2017-09-15 WO PCT/US2017/051912 patent/WO2018053353A1/en not_active Ceased
- 2017-09-15 EP EP17851664.7A patent/EP3512846B1/en active Active
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2019
- 2019-03-14 IL IL265389A patent/IL265389A/en unknown
- 2019-03-14 US US16/353,786 patent/US10730826B2/en active Active
- 2019-03-15 CL CL2019000687A patent/CL2019000687A1/es unknown
- 2019-03-15 PH PH12019500570A patent/PH12019500570A1/en unknown
- 2019-03-27 CO CONC2019/0002950A patent/CO2019002950A2/es unknown
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2020
- 2020-06-11 US US16/899,376 patent/US11325884B2/en active Active
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2022
- 2022-02-11 AU AU2022200927A patent/AU2022200927B2/en active Active
- 2022-05-09 US US17/740,260 patent/US12110263B2/en active Active
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2024
- 2024-10-03 US US18/905,445 patent/US20250270162A1/en active Pending