JP2016530208A5 - - Google Patents
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- Publication number
- JP2016530208A5 JP2016530208A5 JP2016515414A JP2016515414A JP2016530208A5 JP 2016530208 A5 JP2016530208 A5 JP 2016530208A5 JP 2016515414 A JP2016515414 A JP 2016515414A JP 2016515414 A JP2016515414 A JP 2016515414A JP 2016530208 A5 JP2016530208 A5 JP 2016530208A5
- Authority
- JP
- Japan
- Prior art keywords
- cancer
- combination
- methyl
- trifluoromethyl
- phenyl
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims description 32
- 206010028980 Neoplasm Diseases 0.000 claims description 26
- 201000011510 cancer Diseases 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 26
- 239000012453 solvate Substances 0.000 claims description 18
- WXCXUHSOUPDCQV-UHFFFAOYSA-N enzalutamide Chemical compound C1=C(F)C(C(=O)NC)=CC=C1N1C(C)(C)C(=O)N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C1=S WXCXUHSOUPDCQV-UHFFFAOYSA-N 0.000 claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 12
- -1 hydrate Chemical compound 0.000 claims description 12
- 208000032839 leukemia Diseases 0.000 claims description 10
- XTKLTGBKIDQGQL-UHFFFAOYSA-N 2-methyl-1-[[2-methyl-3-(trifluoromethyl)phenyl]methyl]-6-morpholin-4-ylbenzimidazole-4-carboxylic acid Chemical compound CC1=NC2=C(C(O)=O)C=C(N3CCOCC3)C=C2N1CC1=CC=CC(C(F)(F)F)=C1C XTKLTGBKIDQGQL-UHFFFAOYSA-N 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 210000004027 cell Anatomy 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 7
- NAGFMACWWJYORB-UHFFFAOYSA-N 2-fluoro-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC=C1F NAGFMACWWJYORB-UHFFFAOYSA-N 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- 239000007983 Tris buffer Substances 0.000 claims description 6
- 238000002560 therapeutic procedure Methods 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 5
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 208000008839 Kidney Neoplasms Diseases 0.000 claims description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 4
- 206010060862 Prostate cancer Diseases 0.000 claims description 4
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 4
- 206010038389 Renal cancer Diseases 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 208000005017 glioblastoma Diseases 0.000 claims description 4
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 claims description 4
- 201000010982 kidney cancer Diseases 0.000 claims description 4
- 238000012423 maintenance Methods 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- BLIJXOOIHRSQRB-PXYINDEMSA-N n-[(2s)-1-[3-(3-chloro-4-cyanophenyl)pyrazol-1-yl]propan-2-yl]-5-(1-hydroxyethyl)-1h-pyrazole-3-carboxamide Chemical group C([C@H](C)NC(=O)C=1NN=C(C=1)C(C)O)N(N=1)C=CC=1C1=CC=C(C#N)C(Cl)=C1 BLIJXOOIHRSQRB-PXYINDEMSA-N 0.000 claims description 4
- 206010025323 Lymphomas Diseases 0.000 claims description 3
- 208000034578 Multiple myelomas Diseases 0.000 claims description 3
- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
- VVQNAFBGAWCMLU-UHFFFAOYSA-N 1h-benzimidazole-4-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=C1N=CN2 VVQNAFBGAWCMLU-UHFFFAOYSA-N 0.000 claims description 2
- KGKXRSODGHRQDM-UHFFFAOYSA-N 4-[2-methyl-3-[[2-methyl-3-(trifluoromethyl)phenyl]methyl]benzimidazol-5-yl]morpholine Chemical compound Cc1nc2ccc(cc2n1Cc1cccc(c1C)C(F)(F)F)N1CCOCC1 KGKXRSODGHRQDM-UHFFFAOYSA-N 0.000 claims description 2
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims description 2
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims description 2
- 206010003571 Astrocytoma Diseases 0.000 claims description 2
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims description 2
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 2
- 206010005003 Bladder cancer Diseases 0.000 claims description 2
- 206010006187 Breast cancer Diseases 0.000 claims description 2
- 208000026310 Breast neoplasm Diseases 0.000 claims description 2
- 208000011691 Burkitt lymphomas Diseases 0.000 claims description 2
- 206010008342 Cervix carcinoma Diseases 0.000 claims description 2
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 2
- 206010009944 Colon cancer Diseases 0.000 claims description 2
- 208000012609 Cowden disease Diseases 0.000 claims description 2
- 201000002847 Cowden syndrome Diseases 0.000 claims description 2
- 206010014733 Endometrial cancer Diseases 0.000 claims description 2
- 206010014759 Endometrial neoplasm Diseases 0.000 claims description 2
- 206010014967 Ependymoma Diseases 0.000 claims description 2
- 208000031637 Erythroblastic Acute Leukemia Diseases 0.000 claims description 2
- 208000036566 Erythroleukaemia Diseases 0.000 claims description 2
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims description 2
- 208000006168 Ewing Sarcoma Diseases 0.000 claims description 2
- 208000007569 Giant Cell Tumors Diseases 0.000 claims description 2
- 208000032612 Glial tumor Diseases 0.000 claims description 2
- 201000010915 Glioblastoma multiforme Diseases 0.000 claims description 2
- 206010018338 Glioma Diseases 0.000 claims description 2
- 208000005726 Inflammatory Breast Neoplasms Diseases 0.000 claims description 2
- 206010021980 Inflammatory carcinoma of the breast Diseases 0.000 claims description 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 2
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims description 2
- 208000000172 Medulloblastoma Diseases 0.000 claims description 2
- 206010027406 Mesothelioma Diseases 0.000 claims description 2
- 208000003445 Mouth Neoplasms Diseases 0.000 claims description 2
- 208000008770 Multiple Hamartoma Syndrome Diseases 0.000 claims description 2
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims description 2
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 2
- 208000001894 Nasopharyngeal Neoplasms Diseases 0.000 claims description 2
- 206010061306 Nasopharyngeal cancer Diseases 0.000 claims description 2
- 206010029260 Neuroblastoma Diseases 0.000 claims description 2
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims description 2
- 206010030155 Oesophageal carcinoma Diseases 0.000 claims description 2
- 206010033128 Ovarian cancer Diseases 0.000 claims description 2
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 2
- 102000014160 PTEN Phosphohydrolase Human genes 0.000 claims description 2
- 108010011536 PTEN Phosphohydrolase Proteins 0.000 claims description 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 2
- 208000007452 Plasmacytoma Diseases 0.000 claims description 2
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims description 2
- 208000004337 Salivary Gland Neoplasms Diseases 0.000 claims description 2
- 206010061934 Salivary gland cancer Diseases 0.000 claims description 2
- 206010039491 Sarcoma Diseases 0.000 claims description 2
- 208000005718 Stomach Neoplasms Diseases 0.000 claims description 2
- 208000000389 T-cell leukemia Diseases 0.000 claims description 2
- 208000028530 T-cell lymphoblastic leukemia/lymphoma Diseases 0.000 claims description 2
- 206010042971 T-cell lymphoma Diseases 0.000 claims description 2
- 208000027585 T-cell non-Hodgkin lymphoma Diseases 0.000 claims description 2
- 208000024770 Thyroid neoplasm Diseases 0.000 claims description 2
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 2
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 2
- 206010047741 Vulval cancer Diseases 0.000 claims description 2
- 208000004354 Vulvar Neoplasms Diseases 0.000 claims description 2
- 208000008383 Wilms tumor Diseases 0.000 claims description 2
- 208000021841 acute erythroid leukemia Diseases 0.000 claims description 2
- 208000037833 acute lymphoblastic T-cell leukemia Diseases 0.000 claims description 2
- 201000010881 cervical cancer Diseases 0.000 claims description 2
- 230000001684 chronic effect Effects 0.000 claims description 2
- 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims description 2
- 208000029742 colonic neoplasm Diseases 0.000 claims description 2
- 230000002950 deficient Effects 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- 201000004101 esophageal cancer Diseases 0.000 claims description 2
- 201000003444 follicular lymphoma Diseases 0.000 claims description 2
- 206010017758 gastric cancer Diseases 0.000 claims description 2
- 230000002496 gastric effect Effects 0.000 claims description 2
- 201000011243 gastrointestinal stromal tumor Diseases 0.000 claims description 2
- 201000009277 hairy cell leukemia Diseases 0.000 claims description 2
- 201000010536 head and neck cancer Diseases 0.000 claims description 2
- 208000014829 head and neck neoplasm Diseases 0.000 claims description 2
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 2
- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims description 2
- 201000004653 inflammatory breast carcinoma Diseases 0.000 claims description 2
- 208000012987 lip and oral cavity carcinoma Diseases 0.000 claims description 2
- 201000007270 liver cancer Diseases 0.000 claims description 2
- 208000014018 liver neoplasm Diseases 0.000 claims description 2
- 201000005202 lung cancer Diseases 0.000 claims description 2
- 208000020816 lung neoplasm Diseases 0.000 claims description 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 2
- 201000001441 melanoma Diseases 0.000 claims description 2
- 201000008806 mesenchymal cell neoplasm Diseases 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 201000008026 nephroblastoma Diseases 0.000 claims description 2
- 210000000440 neutrophil Anatomy 0.000 claims description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 2
- 201000008968 osteosarcoma Diseases 0.000 claims description 2
- 201000002528 pancreatic cancer Diseases 0.000 claims description 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 2
- 201000009410 rhabdomyosarcoma Diseases 0.000 claims description 2
- 201000011549 stomach cancer Diseases 0.000 claims description 2
- 208000011580 syndromic disease Diseases 0.000 claims description 2
- 201000002510 thyroid cancer Diseases 0.000 claims description 2
- 206010044412 transitional cell carcinoma Diseases 0.000 claims description 2
- 201000005112 urinary bladder cancer Diseases 0.000 claims description 2
- 201000005102 vulva cancer Diseases 0.000 claims description 2
- 230000001154 acute effect Effects 0.000 claims 1
- 239000007972 injectable composition Substances 0.000 claims 1
- 210000003593 megakaryocyte Anatomy 0.000 claims 1
- 239000008247 solid mixture Substances 0.000 claims 1
- 210000001550 testis Anatomy 0.000 claims 1
- 238000000034 method Methods 0.000 description 11
- 102000047934 Caspase-3/7 Human genes 0.000 description 4
- 108700037887 Caspase-3/7 Proteins 0.000 description 4
- 239000002609 medium Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 2
- ZPKCFVXUDUWSBB-UHFFFAOYSA-N 1-morpholin-4-ylbenzimidazole-4-carboxylic acid Chemical compound C1=NC=2C(C(=O)O)=CC=CC=2N1N1CCOCC1 ZPKCFVXUDUWSBB-UHFFFAOYSA-N 0.000 description 1
- 208000036762 Acute promyelocytic leukaemia Diseases 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 208000017604 Hodgkin disease Diseases 0.000 description 1
- 208000021519 Hodgkin lymphoma Diseases 0.000 description 1
- 208000010747 Hodgkins lymphoma Diseases 0.000 description 1
- 208000035490 Megakaryoblastic Acute Leukemia Diseases 0.000 description 1
- 208000024313 Testicular Neoplasms Diseases 0.000 description 1
- 206010057644 Testis cancer Diseases 0.000 description 1
- 208000013593 acute megakaryoblastic leukemia Diseases 0.000 description 1
- 208000020700 acute megakaryocytic leukemia Diseases 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 201000003120 testicular cancer Diseases 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361879895P | 2013-09-19 | 2013-09-19 | |
| US61/879,895 | 2013-09-19 | ||
| PCT/US2014/055816 WO2015042029A1 (en) | 2013-09-19 | 2014-09-16 | Combination drug therapy |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018101120A Division JP6563558B2 (ja) | 2013-09-19 | 2018-05-28 | 組み合わせ薬物療法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016530208A JP2016530208A (ja) | 2016-09-29 |
| JP2016530208A5 true JP2016530208A5 (https=) | 2017-08-24 |
| JP6346944B2 JP6346944B2 (ja) | 2018-06-20 |
Family
ID=52689320
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016515414A Expired - Fee Related JP6346944B2 (ja) | 2013-09-19 | 2014-09-16 | 組み合わせ薬物療法 |
| JP2018101120A Expired - Fee Related JP6563558B2 (ja) | 2013-09-19 | 2018-05-28 | 組み合わせ薬物療法 |
| JP2019135772A Pending JP2019196391A (ja) | 2013-09-19 | 2019-07-24 | 組み合わせ薬物療法 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018101120A Expired - Fee Related JP6563558B2 (ja) | 2013-09-19 | 2018-05-28 | 組み合わせ薬物療法 |
| JP2019135772A Pending JP2019196391A (ja) | 2013-09-19 | 2019-07-24 | 組み合わせ薬物療法 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20160228446A1 (https=) |
| EP (1) | EP3046556A4 (https=) |
| JP (3) | JP6346944B2 (https=) |
| KR (1) | KR20160055911A (https=) |
| CN (1) | CN105530934A (https=) |
| AU (1) | AU2014321456B2 (https=) |
| BR (1) | BR112016005000A8 (https=) |
| CA (1) | CA2921156A1 (https=) |
| RU (1) | RU2016110546A (https=) |
| WO (1) | WO2015042029A1 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2014321456B2 (en) * | 2013-09-19 | 2018-05-24 | Glaxosmithkline Llc | Combination drug therapy |
| US10206949B2 (en) | 2015-09-21 | 2019-02-19 | Ofer Agam | Composition that relieves heartburn, GERD and hangovers |
| US10722484B2 (en) | 2016-03-09 | 2020-07-28 | K-Gen, Inc. | Methods of cancer treatment |
| US20210393651A1 (en) * | 2018-11-09 | 2021-12-23 | Dana-Farber Cancer Institute, Inc. | Targeting the oncogenic transcription factor stat5 with mineralocorticoid analogues |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4644737B2 (ja) * | 2005-05-13 | 2011-03-02 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | ジアリールヒダントイン化合物 |
| US7709517B2 (en) * | 2005-05-13 | 2010-05-04 | The Regents Of The University Of California | Diarylhydantoin compounds |
| JP5198289B2 (ja) * | 2006-02-03 | 2013-05-15 | イムクローン・リミテッド・ライアビリティ・カンパニー | 前立腺癌の治療用アジュバントとしてのｉｇｆ−ｉｒアンタゴニスト |
| LT2656842T (lt) * | 2006-03-27 | 2016-09-26 | The Regents Of The University Of California | Androgeno receptoriaus moduliatorius, skirtas prostatos vėžio ir su androgeno receptoriumi susijusių ligų gydymui |
| PL2538785T3 (pl) * | 2010-02-24 | 2018-08-31 | Medivation Prostate Therapeutics Llc | Sposoby syntezy zwiazków diarylotiohydantoinowych i diarylohydantoinowych |
| JP5719028B2 (ja) * | 2010-10-06 | 2015-05-13 | グラクソスミスクライン エルエルシー | Ｐｉ３キナーゼ阻害剤としてのベンズイミダゾール誘導体 |
| DK2683694T3 (en) * | 2011-03-10 | 2016-07-18 | Suzhou Kintor Pharmaceuticals Inc | ANDROGEN RECEPTOR ANTAGONISTS AND APPLICATIONS THEREOF |
| CN103159680A (zh) * | 2011-12-14 | 2013-06-19 | 爱美尼迪药物有限公司 | 咪唑二酮类化合物及其用途 |
| EP2943199A1 (en) * | 2013-01-09 | 2015-11-18 | Glaxosmithkline Intellectual Property (No. 2) Limited | Combination |
| SG10201907684PA (en) * | 2013-01-15 | 2019-10-30 | Aragon Pharmaceuticals Inc | Androgen receptor modulator and uses thereof |
| AU2014321456B2 (en) * | 2013-09-19 | 2018-05-24 | Glaxosmithkline Llc | Combination drug therapy |
-
2014
- 2014-09-16 AU AU2014321456A patent/AU2014321456B2/en not_active Ceased
- 2014-09-16 CA CA2921156A patent/CA2921156A1/en not_active Abandoned
- 2014-09-16 RU RU2016110546A patent/RU2016110546A/ru not_active Application Discontinuation
- 2014-09-16 EP EP14846138.7A patent/EP3046556A4/en not_active Withdrawn
- 2014-09-16 KR KR1020167009965A patent/KR20160055911A/ko not_active Ceased
- 2014-09-16 BR BR112016005000A patent/BR112016005000A8/pt not_active IP Right Cessation
- 2014-09-16 CN CN201480051583.9A patent/CN105530934A/zh active Pending
- 2014-09-16 JP JP2016515414A patent/JP6346944B2/ja not_active Expired - Fee Related
- 2014-09-16 WO PCT/US2014/055816 patent/WO2015042029A1/en not_active Ceased
- 2014-09-16 US US15/022,561 patent/US20160228446A1/en not_active Abandoned
-
2018
- 2018-05-28 JP JP2018101120A patent/JP6563558B2/ja not_active Expired - Fee Related
-
2019
- 2019-07-24 JP JP2019135772A patent/JP2019196391A/ja active Pending
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