JP2016540828A5 - - Google Patents
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- JP2016540828A5 JP2016540828A5 JP2016553260A JP2016553260A JP2016540828A5 JP 2016540828 A5 JP2016540828 A5 JP 2016540828A5 JP 2016553260 A JP2016553260 A JP 2016553260A JP 2016553260 A JP2016553260 A JP 2016553260A JP 2016540828 A5 JP2016540828 A5 JP 2016540828A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- unsubstituted
- alkyl
- acid
- group
- 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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- 125000000217 alkyl group Chemical group 0.000 claims description 123
- 125000003118 aryl group Chemical group 0.000 claims description 100
- 125000001072 heteroaryl group Chemical group 0.000 claims description 60
- 239000003446 ligand Substances 0.000 claims description 44
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 40
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 40
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 39
- 125000003545 alkoxy group Chemical group 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 32
- 229910052799 carbon Inorganic materials 0.000 claims description 30
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 28
- 125000000623 heterocyclic group Chemical group 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 23
- 239000002184 metal Substances 0.000 claims description 22
- 229910052751 metal Inorganic materials 0.000 claims description 22
- 125000003342 alkenyl group Chemical group 0.000 claims description 20
- 125000000304 alkynyl group Chemical group 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 14
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 claims description 14
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 14
- 235000015165 citric acid Nutrition 0.000 claims description 13
- 208000024827 Alzheimer disease Diseases 0.000 claims description 12
- 208000026072 Motor neurone disease Diseases 0.000 claims description 12
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 12
- 208000005264 motor neuron disease Diseases 0.000 claims description 12
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 claims description 11
- 229940024606 amino acid Drugs 0.000 claims description 11
- 235000001014 amino acid Nutrition 0.000 claims description 11
- 235000012208 gluconic acid Nutrition 0.000 claims description 11
- 239000000174 gluconic acid Substances 0.000 claims description 11
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 10
- 239000000654 additive Substances 0.000 claims description 10
- 229910052802 copper Inorganic materials 0.000 claims description 10
- 239000010949 copper Substances 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- JZRWCGZRTZMZEH-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N JZRWCGZRTZMZEH-UHFFFAOYSA-N 0.000 claims description 10
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 8
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims description 8
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 8
- AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 claims description 8
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 8
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- 125000002252 acyl group Chemical group 0.000 claims description 8
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 8
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 8
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- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 8
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 8
- 229910052742 iron Inorganic materials 0.000 claims description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
- MWZPENIJLUWBSY-VIFPVBQESA-N methyl L-tyrosinate Chemical compound COC(=O)[C@@H](N)CC1=CC=C(O)C=C1 MWZPENIJLUWBSY-VIFPVBQESA-N 0.000 claims description 8
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- 201000002212 progressive supranuclear palsy Diseases 0.000 claims description 8
- LXNHXLLTXMVWPM-UHFFFAOYSA-N pyridoxine Chemical compound CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 claims description 8
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- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 claims description 7
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 claims description 7
- AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 claims description 7
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 claims description 7
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 7
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 claims description 7
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 7
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 claims description 7
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 claims description 7
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- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 claims description 7
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- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 claims description 7
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- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 claims description 7
- 229940116269 uric acid Drugs 0.000 claims description 7
- ODJQKYXPKWQWNK-UHFFFAOYSA-N 3,3'-Thiobispropanoic acid Chemical compound OC(=O)CCSCCC(O)=O ODJQKYXPKWQWNK-UHFFFAOYSA-N 0.000 claims description 6
- OCUCCJIRFHNWBP-IYEMJOQQSA-L Copper gluconate Chemical group [Cu+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O OCUCCJIRFHNWBP-IYEMJOQQSA-L 0.000 claims description 6
- ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 claims description 6
- 201000011240 Frontotemporal dementia Diseases 0.000 claims description 6
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Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2099441A4 (en) | 2006-11-20 | 2010-04-28 | Univ Melbourne | METAL DISPENSER AND ITS THERAPEUTIC USES |
| US10413554B2 (en) * | 2006-11-20 | 2019-09-17 | The University Of Melbourne | Metal delivery agents and therapeutic uses of the same |
| US11142835B2 (en) | 2016-06-10 | 2021-10-12 | University Of Louisville Research Foundation, Inc. | Compounds, their preparation, related compositions, catalysts, electrochemical cells, fuel cells, and uses thereof |
| US11208379B2 (en) | 2017-05-04 | 2021-12-28 | University Of Louisville Research Foundation, Inc. | Compounds, compositions, methods for treating diseases, and methods for preparing compounds |
| IL272895B2 (en) * | 2017-09-01 | 2025-06-01 | Univ Oregon State | Therapeutic metal complexes and ligands and methods of making and using same |
| CN108129522A (zh) * | 2018-01-05 | 2018-06-08 | 广西师范学院 | 酞菁连芳基钌化合物及其用途和制备方法 |
| AU2019423049C1 (en) * | 2019-01-16 | 2023-08-31 | Shenzhen Profound View Pharmaceutical Technology Co., Ltd. | Copper nanoclusters, thymine-modified hyaluronic acid and poly (copper nanoclusters), method for preparing the same, and application thereof |
| MX2022001037A (es) * | 2019-07-25 | 2022-07-19 | Als Therapy Development Inst | Cuptsm para el tratamiento de trastornos neurodegenerativos. |
| JP2022546700A (ja) * | 2019-08-30 | 2022-11-07 | リサーチ インスティチュート アット ネイションワイド チルドレンズ ホスピタル | ミトコンドリア機能障害に関連する神経変性障害の治療のための銅－ａｔｓｍ |
| EP4025223A4 (en) * | 2019-09-03 | 2024-01-03 | Procypra Therapeutics, LLC | NEW POLYMORPH AND ITS USES |
| CN111747845B (zh) * | 2020-06-24 | 2022-11-01 | 中南民族大学 | 一种可见光催化选择性氧化葡萄糖的方法 |
| AR123360A1 (es) * | 2020-08-26 | 2022-11-23 | Als Therapy Development Inst | Complejos de cobre para el tratamiento de trastornos neurodegenerativos |
| CN112999243B (zh) * | 2021-03-05 | 2022-07-29 | 北京工业大学 | 金络合物在制备预防和/或治疗多发性硬化症的药物中的应用 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5716895A (en) * | 1980-07-05 | 1982-01-28 | Otsuka Chem Co Ltd | Platinum 2 complex and antitumor agent containing the same as active principle |
| US5707604A (en) * | 1986-11-18 | 1998-01-13 | Access Pharmaceuticals, Inc. | Vivo agents comprising metal-ion chelates with acidic saccharides and glycosaminoglycans, giving improved site-selective localization, uptake mechanism, sensitivity and kinetic-spatial profiles |
| JPH10101566A (ja) * | 1996-09-27 | 1998-04-21 | Kagaku Gijutsu Shinko Jigyodan | 網膜保護剤 |
| EP1250587A1 (en) | 2000-01-28 | 2002-10-23 | Pion, Inc. | MEASUREMENT OF SOLUBILITY-pH PROFILES |
| JP2007524596A (ja) | 2003-02-28 | 2007-08-30 | トランスフォーム・ファーマシューティカルズ・インコーポレイテッド | 共結晶医薬組成物 |
| EP2099441A4 (en) * | 2006-11-20 | 2010-04-28 | Univ Melbourne | METAL DISPENSER AND ITS THERAPEUTIC USES |
| CN102317257B (zh) * | 2008-12-12 | 2015-08-26 | 墨尔本大学 | 制备不对称双(缩氨基硫脲)的方法 |
| AU2013249307B2 (en) | 2012-04-17 | 2017-11-09 | Merrimack Pharmaceuticals, Inc. | Compositions and methods for non-invasive imaging |
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- 2014-11-10 JP JP2016553260A patent/JP6619348B2/ja not_active Expired - Fee Related
- 2014-11-10 CN CN201480072886.9A patent/CN105899519B/zh not_active Expired - Fee Related
- 2014-11-10 WO PCT/US2014/064879 patent/WO2015070177A2/en not_active Ceased
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