JP2005518453A5 - - Google Patents
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- JP2005518453A5 JP2005518453A5 JP2003571422A JP2003571422A JP2005518453A5 JP 2005518453 A5 JP2005518453 A5 JP 2005518453A5 JP 2003571422 A JP2003571422 A JP 2003571422A JP 2003571422 A JP2003571422 A JP 2003571422A JP 2005518453 A5 JP2005518453 A5 JP 2005518453A5
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- JP
- Japan
- Prior art keywords
- tcro
- cation
- compound
- mammal
- 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.)
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- 150000001768 cations Chemical group 0.000 claims 46
- 150000001875 compounds Chemical class 0.000 claims 44
- 238000000034 method Methods 0.000 claims 42
- 150000001747 carotenoids Chemical group 0.000 claims 23
- 241000124008 Mammalia Species 0.000 claims 20
- RMDMBHQVNHQDDD-VFWKRBOSSA-L disodium;(2e,4e,6e,8e,10e,12e,14e)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioate Chemical compound [Na+].[Na+].[O-]C(=O)C(/C)=C/C=C/C(/C)=C/C=C/C=C(\C)/C=C/C=C(\C)C([O-])=O RMDMBHQVNHQDDD-VFWKRBOSSA-L 0.000 claims 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 9
- 229910052736 halogen Inorganic materials 0.000 claims 8
- 150000002367 halogens Chemical class 0.000 claims 8
- 239000000243 solution Substances 0.000 claims 7
- 235000021466 carotenoid Nutrition 0.000 claims 6
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 5
- 230000003381 solubilizing effect Effects 0.000 claims 5
- 239000002904 solvent Substances 0.000 claims 4
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 claims 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 3
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 239000002585 base Substances 0.000 claims 3
- 238000005859 coupling reaction Methods 0.000 claims 3
- 150000005690 diesters Chemical class 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- AYODHZHFDRRQEZ-XLKYRCCQSA-N (2e,4e,6e)-2,7-dimethylocta-2,4,6-trienedial Chemical group O=CC(/C)=C/C=C/C=C(\C)C=O AYODHZHFDRRQEZ-XLKYRCCQSA-N 0.000 claims 2
- FXJVNINSOKCNJP-UHFFFAOYSA-N 4-methylbenzenesulfinic acid Chemical compound CC1=CC=C(S(O)=O)C=C1 FXJVNINSOKCNJP-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 230000008878 coupling Effects 0.000 claims 2
- 238000010168 coupling process Methods 0.000 claims 2
- 238000009792 diffusion process Methods 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 206010048962 Brain oedema Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 208000002249 Diabetes Complications Diseases 0.000 claims 1
- 206010012655 Diabetic complications Diseases 0.000 claims 1
- 206010014561 Emphysema Diseases 0.000 claims 1
- 208000032456 Hemorrhagic Shock Diseases 0.000 claims 1
- 206010021143 Hypoxia Diseases 0.000 claims 1
- 206010049771 Shock haemorrhagic Diseases 0.000 claims 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 1
- 208000029033 Spinal Cord disease Diseases 0.000 claims 1
- 208000030886 Traumatic Brain injury Diseases 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 239000003637 basic solution Substances 0.000 claims 1
- 208000006752 brain edema Diseases 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000008367 deionised water Substances 0.000 claims 1
- 229910021641 deionized water Inorganic materials 0.000 claims 1
- 150000001983 dialkylethers Chemical class 0.000 claims 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical group OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 claims 1
- 230000002708 enhancing effect Effects 0.000 claims 1
- 230000007954 hypoxia Effects 0.000 claims 1
- 208000028867 ischemia Diseases 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 229910021645 metal ion Inorganic materials 0.000 claims 1
- KTUPSHQCXGWFMG-UHFFFAOYSA-N methyl 2-methyl-4-(triphenyl-$l^{5}-phosphanylidene)but-2-enoate Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC=C(C)C(=O)OC)C1=CC=CC=C1 KTUPSHQCXGWFMG-UHFFFAOYSA-N 0.000 claims 1
- 150000004712 monophosphates Chemical group 0.000 claims 1
- 150000002892 organic cations Chemical class 0.000 claims 1
- 208000003154 papilloma Diseases 0.000 claims 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 1
- 208000023504 respiratory system disease Diseases 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 230000009529 traumatic brain injury Effects 0.000 claims 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical compound C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 claims 1
- 125000002264 triphosphate group Chemical group [H]OP(=O)(O[H])OP(=O)(O[H])OP(=O)(O[H])O* 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35871802P | 2002-02-25 | 2002-02-25 | |
| PCT/US2003/005521 WO2003072734A2 (en) | 2002-02-25 | 2003-02-25 | Bipolar trans carotenoid salts and their uses |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009274988A Division JP2010106029A (ja) | 2002-02-25 | 2009-12-02 | 二極性トランスカロテノイド塩およびそれらの使用 |
| JP2010110185A Division JP2010229137A (ja) | 2002-02-25 | 2010-05-12 | 二極性トランスカロテノイド塩およびそれらの使用 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005518453A JP2005518453A (ja) | 2005-06-23 |
| JP2005518453A5 true JP2005518453A5 (https=) | 2005-12-22 |
Family
ID=27765977
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003571422A Withdrawn JP2005518453A (ja) | 2002-02-25 | 2003-02-25 | 二極性トランスカロテノイド塩およびそれらの使用 |
| JP2009274988A Pending JP2010106029A (ja) | 2002-02-25 | 2009-12-02 | 二極性トランスカロテノイド塩およびそれらの使用 |
| JP2010110185A Withdrawn JP2010229137A (ja) | 2002-02-25 | 2010-05-12 | 二極性トランスカロテノイド塩およびそれらの使用 |
| JP2013197629A Expired - Fee Related JP5774655B2 (ja) | 2002-02-25 | 2013-09-24 | 二極性トランスカロテノイド塩およびそれらの使用 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009274988A Pending JP2010106029A (ja) | 2002-02-25 | 2009-12-02 | 二極性トランスカロテノイド塩およびそれらの使用 |
| JP2010110185A Withdrawn JP2010229137A (ja) | 2002-02-25 | 2010-05-12 | 二極性トランスカロテノイド塩およびそれらの使用 |
| JP2013197629A Expired - Fee Related JP5774655B2 (ja) | 2002-02-25 | 2013-09-24 | 二極性トランスカロテノイド塩およびそれらの使用 |
Country Status (19)
| Country | Link |
|---|---|
| US (4) | US7351844B2 (https=) |
| EP (1) | EP1487774B1 (https=) |
| JP (4) | JP2005518453A (https=) |
| KR (1) | KR101020115B1 (https=) |
| CN (1) | CN1671643B (https=) |
| AU (1) | AU2003215396B2 (https=) |
| BR (1) | BR0307935A (https=) |
| CA (1) | CA2477245A1 (https=) |
| CZ (1) | CZ2004904A3 (https=) |
| EA (1) | EA200401111A1 (https=) |
| HU (1) | HUP0500134A3 (https=) |
| IL (1) | IL163685A0 (https=) |
| MX (1) | MXPA04008253A (https=) |
| NO (1) | NO20043661L (https=) |
| NZ (2) | NZ564486A (https=) |
| PL (1) | PL373780A1 (https=) |
| UA (1) | UA83341C2 (https=) |
| WO (1) | WO2003072734A2 (https=) |
| ZA (1) | ZA200406673B (https=) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7759506B2 (en) | 2002-02-25 | 2010-07-20 | Diffusion Pharmaceuticals Llc | Bipolar trans carotenoid salts and their uses |
| CA2477245A1 (en) * | 2002-02-25 | 2003-09-04 | Diffusion Pharmaceuticals Llc | Bipolar trans carotenoid salts and their uses |
| AU2011265546B2 (en) * | 2003-08-25 | 2016-05-12 | Diffusion Pharmaceuticals Llc | Bipolar Trans Carotenoid Salts and Their Uses |
| CA2537210C (en) * | 2003-08-25 | 2013-06-04 | Diffusion Pharmaceuticals Llc | Bipolar trans carotenoid salts and their uses |
| EP2540696B1 (en) * | 2005-02-24 | 2020-01-01 | Diffusion Pharmaceuticals LLC | Trans carotenoids, formulation and uses |
| JPWO2006112283A1 (ja) * | 2005-04-13 | 2008-12-11 | 理研ビタミン株式会社 | 抗疲労剤 |
| EP1965807A4 (en) * | 2005-11-23 | 2010-10-27 | Epix Delaware Inc | S1P RECEPTOR MODULATING COMPOUNDS AND THEIR USE |
| US20070288322A1 (en) * | 2006-05-23 | 2007-12-13 | Toshiba Tec Kabushiki Kaisha | Portable terminal and its programs, settlement apparatus, and merchandising information providing apparatus |
| CN101687757A (zh) | 2007-04-13 | 2010-03-31 | 扩散药品有限公司 | 双极性反式类胡萝卜素作为预治疗及其在周围血管疾病的治疗中的应用 |
| CA2688837A1 (en) * | 2007-06-19 | 2008-12-24 | Novartis Ag | Organic compounds |
| KR20100083820A (ko) | 2007-10-31 | 2010-07-22 | 디퓨젼 파마슈티컬즈 엘엘씨 | 저분자 확산을 촉진시키는 신규한 치료요법 |
| CN101157645B (zh) * | 2007-11-27 | 2010-06-02 | 江南大学 | 一种藏红花酸的合成方法 |
| EP2445339B1 (en) | 2009-06-22 | 2019-08-07 | Diffusion Pharmaceuticals LLC | Diffusion enhancing compound and its use with a thrombolytic |
| JP2010090151A (ja) * | 2009-12-09 | 2010-04-22 | Diffusion Pharmaceuticals Llc | 双極性トランスカロテノイド塩及びそれらの使用 |
| AU2011262361A1 (en) | 2010-06-02 | 2013-01-10 | Diffusion Pharmaceuticals Llc | Oral formulations of bipolar trans carotenoids |
| CN101967087A (zh) * | 2010-09-21 | 2011-02-09 | 上海大学 | (e)- 4.4-二甲氧基-2-丁烯醛的制备方法 |
| CN103172504B (zh) * | 2011-12-26 | 2014-10-08 | 南京工业大学 | 2,7-二甲基-2,4,6-辛三烯-1,8-二醛的合成方法 |
| CA3018550A1 (en) | 2016-03-24 | 2017-09-28 | Diffusion Pharmaceuticals Llc | Use of bipolar trans carotenoids with chemotherapy and radiotherapy for treatment of cancer |
| JP7355394B2 (ja) | 2018-05-03 | 2023-10-03 | エル．イー．エー．エフ． ホールディングス グループ エルエルシー | カロテノイド組成物およびその使用 |
| WO2021207690A1 (en) * | 2020-04-09 | 2021-10-14 | L.E.A.F. Holdings Group Llc | Trans-crocetin compositions and treatment regimens |
| WO2021207650A1 (en) * | 2020-04-09 | 2021-10-14 | L.E.A.F. Holdings Group Llc | Trans-crocetin compositions and treatment regimens |
| US20240316000A1 (en) * | 2021-06-29 | 2024-09-26 | Diffusion Pharmaceuticals Llc | Methods of treatment |
| WO2023081779A1 (en) * | 2021-11-03 | 2023-05-11 | Diffusion Pharmaceuticals Llc | Crystalline forms of a diffusion enhancing compound |
| CN114534729B (zh) * | 2022-03-07 | 2024-05-03 | 万华化学集团股份有限公司 | 一种催化剂及其制备方法和其在电化学法制备β-胡萝卜素中的应用 |
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| RU2265434C2 (ru) | 2003-09-30 | 2005-12-10 | Государственное учреждение Научно-исследовательский Институт Общей реаниматологии Российской Академии Медицинских Наук (ГУ НИИ ОР РАМН) | Способ лечения острого респираторного дистресс-синдрома |
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-
2003
- 2003-02-25 CA CA002477245A patent/CA2477245A1/en not_active Abandoned
- 2003-02-25 EA EA200401111A patent/EA200401111A1/ru unknown
- 2003-02-25 HU HU0500134A patent/HUP0500134A3/hu unknown
- 2003-02-25 BR BR0307935-0A patent/BR0307935A/pt not_active IP Right Cessation
- 2003-02-25 NZ NZ564486A patent/NZ564486A/en not_active IP Right Cessation
- 2003-02-25 KR KR1020047013118A patent/KR101020115B1/ko not_active Expired - Fee Related
- 2003-02-25 AU AU2003215396A patent/AU2003215396B2/en not_active Ceased
- 2003-02-25 NZ NZ535323A patent/NZ535323A/en not_active IP Right Cessation
- 2003-02-25 UA UA20040807055A patent/UA83341C2/uk unknown
- 2003-02-25 JP JP2003571422A patent/JP2005518453A/ja not_active Withdrawn
- 2003-02-25 PL PL03373780A patent/PL373780A1/xx not_active Application Discontinuation
- 2003-02-25 CN CN038045664A patent/CN1671643B/zh not_active Expired - Fee Related
- 2003-02-25 WO PCT/US2003/005521 patent/WO2003072734A2/en not_active Ceased
- 2003-02-25 EP EP03711221.6A patent/EP1487774B1/en not_active Expired - Lifetime
- 2003-02-25 CZ CZ2004904A patent/CZ2004904A3/cs unknown
- 2003-02-25 US US10/372,717 patent/US7351844B2/en not_active Expired - Lifetime
- 2003-02-25 MX MXPA04008253A patent/MXPA04008253A/es active IP Right Grant
- 2003-02-25 IL IL16368503A patent/IL163685A0/xx unknown
-
2004
- 2004-08-23 ZA ZA200406673A patent/ZA200406673B/en unknown
- 2004-09-01 NO NO20043661A patent/NO20043661L/no not_active Application Discontinuation
-
2007
- 2007-03-19 US US11/723,383 patent/US20070161610A1/en not_active Abandoned
- 2007-04-27 US US11/790,779 patent/US8269027B2/en not_active Expired - Fee Related
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2009
- 2009-12-02 JP JP2009274988A patent/JP2010106029A/ja active Pending
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2010
- 2010-05-12 JP JP2010110185A patent/JP2010229137A/ja not_active Withdrawn
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2012
- 2012-09-17 US US13/621,650 patent/US20140051759A1/en not_active Abandoned
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2013
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