JP2020511450A5 - - Google Patents
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- Publication number
- JP2020511450A5 JP2020511450A5 JP2019548696A JP2019548696A JP2020511450A5 JP 2020511450 A5 JP2020511450 A5 JP 2020511450A5 JP 2019548696 A JP2019548696 A JP 2019548696A JP 2019548696 A JP2019548696 A JP 2019548696A JP 2020511450 A5 JP2020511450 A5 JP 2020511450A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- iia
- pharmaceutically acceptable
- iiia
- formula
- 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.)
- Pending
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- 150000001875 compounds Chemical class 0.000 claims 25
- 150000003839 salts Chemical class 0.000 claims 14
- 239000012453 solvate Substances 0.000 claims 11
- 239000008194 pharmaceutical composition Substances 0.000 claims 9
- 229910052760 oxygen Inorganic materials 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 5
- 125000003282 alkyl amino group Chemical group 0.000 claims 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 4
- 125000004103 aminoalkyl group Chemical group 0.000 claims 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 125000001188 haloalkyl group Chemical group 0.000 claims 4
- 125000001475 halogen functional group Chemical group 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- 208000010125 myocardial infarction Diseases 0.000 claims 4
- -1 nitro, carboxy Chemical group 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 239000003642 reactive oxygen metabolite Substances 0.000 claims 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000028867 ischemia Diseases 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 2
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 2
- 206010048610 Cardiotoxicity Diseases 0.000 claims 2
- 201000006306 Cor pulmonale Diseases 0.000 claims 2
- 206010014523 Embolism and thrombosis Diseases 0.000 claims 2
- 206010019280 Heart failures Diseases 0.000 claims 2
- 206010064911 Pulmonary arterial hypertension Diseases 0.000 claims 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical group [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 2
- 231100000259 cardiotoxicity Toxicity 0.000 claims 2
- IWBBKLMHAILHAR-UHFFFAOYSA-N chembl402341 Chemical compound C1=CC(O)=CC=C1C1=CC(=S)SS1 IWBBKLMHAILHAR-UHFFFAOYSA-N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 210000003470 mitochondria Anatomy 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 239000007800 oxidant agent Substances 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- FZNSULGQTRGDDF-UHFFFAOYSA-N 4-(4-hydroxyphenyl)dithiole-3-thione Chemical compound C1=CC(O)=CC=C1C1=CSSC1=S FZNSULGQTRGDDF-UHFFFAOYSA-N 0.000 claims 1
- GEOXNKHTZAUVBM-UHFFFAOYSA-N 4-(5-hydroxyiminodithiol-3-yl)phenol Chemical compound OC1=CC=C(C=C1)C1=CC(SS1)=NO GEOXNKHTZAUVBM-UHFFFAOYSA-N 0.000 claims 1
- KDJVJTMHWXZZJJ-UHFFFAOYSA-N 5-(1-benzofuran-5-yl)dithiole-3-thione Chemical compound O1C=CC2=C1C=CC(=C2)C1=CC(SS1)=S KDJVJTMHWXZZJJ-UHFFFAOYSA-N 0.000 claims 1
- HLFFXEFJKQLPTQ-UHFFFAOYSA-N 5-(4-hydroxyphenyl)-1,2,4-dithiazole-3-thione Chemical compound OC1=CC=C(C=C1)C1=NC(SS1)=S HLFFXEFJKQLPTQ-UHFFFAOYSA-N 0.000 claims 1
- XXDYQIINMXOSSO-UHFFFAOYSA-N 5-(4-hydroxyphenyl)dithiol-3-one Chemical compound C1=CC(O)=CC=C1C1=CC(=O)SS1 XXDYQIINMXOSSO-UHFFFAOYSA-N 0.000 claims 1
- MYTUEHUXUXSJCN-UHFFFAOYSA-N 5-(5-sulfanylidenedithiol-3-yl)-3H-1,3-benzoxazol-2-one Chemical compound OC=1OC2=C(N=1)C=C(C=C2)C1=CC(SS1)=S MYTUEHUXUXSJCN-UHFFFAOYSA-N 0.000 claims 1
- CMAFOEYOQDEIOR-UHFFFAOYSA-N 6-(5-sulfanylidenedithiol-3-yl)-3H-1,3-benzothiazol-2-one Chemical compound OC1=NC2=CC=C(C=C2S1)C1=CC(=S)SS1 CMAFOEYOQDEIOR-UHFFFAOYSA-N 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 208000031229 Cardiomyopathies Diseases 0.000 claims 1
- 208000035473 Communicable disease Diseases 0.000 claims 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 208000019693 Lung disease Diseases 0.000 claims 1
- 208000029578 Muscle disease Diseases 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 208000025966 Neurological disease Diseases 0.000 claims 1
- 206010034010 Parkinsonism Diseases 0.000 claims 1
- 206010063837 Reperfusion injury Diseases 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 230000032683 aging Effects 0.000 claims 1
- 206010061592 cardiac fibrillation Diseases 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 208000012947 ischemia reperfusion injury Diseases 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 208000017169 kidney disease Diseases 0.000 claims 1
- 208000019423 liver disease Diseases 0.000 claims 1
- 210000004072 lung Anatomy 0.000 claims 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical group [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims 1
- 229910052753 mercury Inorganic materials 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- TZVDSZGVPRAWHE-UHFFFAOYSA-N methyl 5-(5-sulfanylidenedithiol-3-yl)indole-1-carboxylate Chemical compound S=C1SSC(=C1)C=1C=C2C=CN(C2=CC=1)C(=O)OC TZVDSZGVPRAWHE-UHFFFAOYSA-N 0.000 claims 1
- 230000002438 mitochondrial effect Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000005429 oxyalkyl group Chemical group 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 208000030087 premature aging syndrome Diseases 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 235000017281 sodium acetate Nutrition 0.000 claims 1
- 239000001632 sodium acetate Substances 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 0 CC=*[C@]1*c2c(**)c(C3=CNNC3=*)c(*)c(*)c2*1 Chemical compound CC=*[C@]1*c2c(**)c(C3=CNNC3=*)c(*)c(*)c2*1 0.000 description 2
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762467874P | 2017-03-07 | 2017-03-07 | |
| EP17159691 | 2017-03-07 | ||
| US62/467,874 | 2017-03-07 | ||
| EP17159691.9 | 2017-03-07 | ||
| PCT/EP2018/055651 WO2018162581A1 (en) | 2017-03-07 | 2018-03-07 | Desmethylanethole trithione derivatives for the treatment of diseases linked to mitochondrial reactive oxygen species (ros) production |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2020511450A JP2020511450A (ja) | 2020-04-16 |
| JP2020511450A5 true JP2020511450A5 (enExample) | 2021-04-15 |
Family
ID=61628329
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019548696A Pending JP2020511450A (ja) | 2017-03-07 | 2018-03-07 | ミトコンドリアの活性酸素種（ｒｏｓ）産生に関連する疾患の治療のためのデスメチルアネトールトリチオン誘導体 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US11484529B2 (enExample) |
| EP (1) | EP3592348A1 (enExample) |
| JP (1) | JP2020511450A (enExample) |
| KR (1) | KR20190129900A (enExample) |
| CN (1) | CN110662535A (enExample) |
| AU (1) | AU2018232799B2 (enExample) |
| BR (1) | BR112019018495A2 (enExample) |
| CA (1) | CA3055122A1 (enExample) |
| IL (1) | IL269127A (enExample) |
| RU (1) | RU2019131478A (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113038969A (zh) * | 2018-09-06 | 2021-06-25 | Op2药品公司 | 包含茴三硫或其衍生物的环糊精复合物的药物组合物 |
| CN112546216B (zh) * | 2020-11-20 | 2022-10-28 | 西湖大学 | 小分子化合物奥替普拉在制备增强体液免疫应答的药物中的应用 |
| EP4259124A1 (en) * | 2020-12-10 | 2023-10-18 | Marin, Frédéric | Anethole trithione administration regimen for the prevention or treatment of ischemia-reperfusion injuries |
| CN116848101A (zh) * | 2021-02-09 | 2023-10-03 | 勃林格殷格翰国际有限公司 | 复合体i的调节剂 |
| CN114414332B (zh) * | 2022-01-05 | 2024-04-16 | 北京科技大学 | 一种基于Al-CQDs和Al-CNSs的抗氧化剂的制备方法 |
| CN119185368A (zh) * | 2024-09-26 | 2024-12-27 | 中南大学 | 具有线粒体序贯靶向能力的强抗氧化性纳米药物及其制备方法和应用 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU5474198A (en) | 1996-12-24 | 1998-07-17 | National Research Council Of Canada | Treatment of diseases or prevention of cellular damage caused by oxygen-containing free radicals |
| WO2001009118A2 (en) * | 1999-07-29 | 2001-02-08 | Patrick T Prendergast | Dithiolthione compounds for the treatment of neurological disorders and for memory enhancement |
| KR20030067935A (ko) | 2002-02-09 | 2003-08-19 | 김상건 | 올티프라즈를 포함하는 간경화(간경변증) 치료를 위한 간 조직 재생용 제약 조성물 |
| EP1288940B1 (en) * | 2000-05-22 | 2009-12-02 | Clarion Co., Ltd. | Disk player |
| CN1355156A (zh) * | 2000-11-27 | 2002-06-26 | 朱国和 | 含有造纸废料污泥的微生物菌肥及其制备方法 |
| CN1244325C (zh) | 2001-05-11 | 2006-03-08 | 成都国嘉联合制药有限公司 | 胆维他在制药中的应用 |
| US7199122B2 (en) | 2001-10-02 | 2007-04-03 | Fox Chase Cancer Center | Methods for inhibiting angiogenesis |
| US20050182128A1 (en) | 2002-02-13 | 2005-08-18 | Stephen Lam | Use of anethole dithiolethione in lung cancer chemoprevention |
| TW200640898A (en) | 2005-02-24 | 2006-12-01 | Solvay Pharm Bv | Anethole dithiolethione and other dithiolethiones for the treatment of conditions associated with dysfunction of monoamine neurotransmission |
| EP2125775A4 (en) | 2007-03-01 | 2011-07-13 | Cedars Sinai Medical Center | ANTIOXIDATION POLYMERS WITH [1,2] -DITHIOLANTEILES AND THEIR USE |
| CN102807557B (zh) | 2012-08-21 | 2015-02-04 | 苏州大学 | 3h-1,2-二硫环戊烯-3-硫酮类化合物及其应用 |
| CN102961376B (zh) * | 2012-11-06 | 2015-06-10 | 暨南大学 | HMG-CoA还原酶抑制剂氟伐他汀在制备抗淋巴瘤药物中的应用 |
| CN102961375B (zh) | 2012-12-05 | 2015-01-14 | 苏州大学 | 一种ampk激活剂及其在制备治疗糖尿病和/或糖尿病并发症的药物中的应用 |
-
2018
- 2018-03-07 BR BR112019018495A patent/BR112019018495A2/pt not_active IP Right Cessation
- 2018-03-07 JP JP2019548696A patent/JP2020511450A/ja active Pending
- 2018-03-07 RU RU2019131478A patent/RU2019131478A/ru unknown
- 2018-03-07 KR KR1020197028579A patent/KR20190129900A/ko not_active Ceased
- 2018-03-07 EP EP18711055.6A patent/EP3592348A1/en not_active Withdrawn
- 2018-03-07 CA CA3055122A patent/CA3055122A1/en active Pending
- 2018-03-07 US US16/491,617 patent/US11484529B2/en active Active
- 2018-03-07 CN CN201880029927.4A patent/CN110662535A/zh active Pending
- 2018-03-07 AU AU2018232799A patent/AU2018232799B2/en not_active Ceased
-
2019
- 2019-09-04 IL IL26912719A patent/IL269127A/en unknown