JP2020509095A5 - - Google Patents
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- JP2020509095A5 JP2020509095A5 JP2019569659A JP2019569659A JP2020509095A5 JP 2020509095 A5 JP2020509095 A5 JP 2020509095A5 JP 2019569659 A JP2019569659 A JP 2019569659A JP 2019569659 A JP2019569659 A JP 2019569659A JP 2020509095 A5 JP2020509095 A5 JP 2020509095A5
- Authority
- JP
- Japan
- Prior art keywords
- acid
- preparation according
- formulation
- cancer
- lipophilic
- 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
Links
- 238000002360 preparation method Methods 0.000 claims 14
- 238000009472 formulation Methods 0.000 claims 10
- 239000000203 mixture Substances 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 3
- 150000002632 lipids Chemical class 0.000 claims 3
- 239000003381 stabilizer Substances 0.000 claims 3
- 239000004094 surface-active agent Substances 0.000 claims 3
- YWWVWXASSLXJHU-AATRIKPKSA-N (9E)-tetradecenoic acid Chemical compound CCCC\C=C\CCCCCCCC(O)=O YWWVWXASSLXJHU-AATRIKPKSA-N 0.000 claims 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 claims 2
- 150000007942 carboxylates Chemical class 0.000 claims 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims 2
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 claims 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims 2
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 claims 2
- BITHHVVYSMSWAG-KTKRTIGZSA-N (11Z)-icos-11-enoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCC(O)=O BITHHVVYSMSWAG-KTKRTIGZSA-N 0.000 claims 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 claims 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims 1
- YWWVWXASSLXJHU-UHFFFAOYSA-N 9E-tetradecenoic acid Natural products CCCCC=CCCCCCCCC(O)=O YWWVWXASSLXJHU-UHFFFAOYSA-N 0.000 claims 1
- 206010005003 Bladder cancer Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 claims 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 239000005639 Lauric acid Substances 0.000 claims 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- 208000034578 Multiple myelomas Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 206010052399 Neuroendocrine tumour Diseases 0.000 claims 1
- 239000005642 Oleic acid Substances 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 235000021319 Palmitoleic acid Nutrition 0.000 claims 1
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 208000006265 Renal cell carcinoma Diseases 0.000 claims 1
- BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 claims 1
- 235000021355 Stearic acid Nutrition 0.000 claims 1
- AOBORMOPSGHCAX-UHFFFAOYSA-N Tocophersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-UHFFFAOYSA-N 0.000 claims 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 1
- UWHZIFQPPBDJPM-FPLPWBNLSA-M Vaccenic acid Natural products CCCCCC\C=C/CCCCCCCCCC([O-])=O UWHZIFQPPBDJPM-FPLPWBNLSA-M 0.000 claims 1
- 235000021322 Vaccenic acid Nutrition 0.000 claims 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 claims 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 claims 1
- 239000003963 antioxidant agent Substances 0.000 claims 1
- 230000003078 antioxidant effect Effects 0.000 claims 1
- 229940114079 arachidonic acid Drugs 0.000 claims 1
- 235000021342 arachidonic acid Nutrition 0.000 claims 1
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 claims 1
- 159000000007 calcium salts Chemical class 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 235000014113 dietary fatty acids Nutrition 0.000 claims 1
- 229940108623 eicosenoic acid Drugs 0.000 claims 1
- BITHHVVYSMSWAG-UHFFFAOYSA-N eicosenoic acid Natural products CCCCCCCCC=CCCCCCCCCCC(O)=O BITHHVVYSMSWAG-UHFFFAOYSA-N 0.000 claims 1
- 239000000194 fatty acid Substances 0.000 claims 1
- 229930195729 fatty acid Natural products 0.000 claims 1
- -1 fatty acid carboxylate salt Chemical class 0.000 claims 1
- 208000005017 glioblastoma Diseases 0.000 claims 1
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 claims 1
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 claims 1
- 201000010536 head and neck cancer Diseases 0.000 claims 1
- 208000014829 head and neck neoplasm Diseases 0.000 claims 1
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims 1
- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 235000020778 linoleic acid Nutrition 0.000 claims 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims 1
- 229960004488 linolenic acid Drugs 0.000 claims 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 claims 1
- 210000004072 lung Anatomy 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 229960003511 macrogol Drugs 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 208000016065 neuroendocrine neoplasm Diseases 0.000 claims 1
- 201000011519 neuroendocrine tumor Diseases 0.000 claims 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims 1
- 229960002446 octanoic acid Drugs 0.000 claims 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical class CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims 1
- 229940113116 polyethylene glycol 1000 Drugs 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 208000015347 renal cell adenocarcinoma Diseases 0.000 claims 1
- NNNVXFKZMRGJPM-KHPPLWFESA-N sapienic acid Chemical compound CCCCCCCCC\C=C/CCCCC(O)=O NNNVXFKZMRGJPM-KHPPLWFESA-N 0.000 claims 1
- 208000000649 small cell carcinoma Diseases 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000001509 sodium citrate Substances 0.000 claims 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000008117 stearic acid Substances 0.000 claims 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- UWHZIFQPPBDJPM-BQYQJAHWSA-N trans-vaccenic acid Chemical compound CCCCCC\C=C\CCCCCCCCCC(O)=O UWHZIFQPPBDJPM-BQYQJAHWSA-N 0.000 claims 1
- 150000003626 triacylglycerols Chemical class 0.000 claims 1
- 201000005112 urinary bladder cancer Diseases 0.000 claims 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2023045166A JP2023088988A (ja) | 2017-03-03 | 2023-03-22 | 改善された安定性を有する製剤 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762466955P | 2017-03-03 | 2017-03-03 | |
| US62/466,955 | 2017-03-03 | ||
| PCT/US2018/020797 WO2018161054A1 (en) | 2017-03-03 | 2018-03-02 | Formulations with improved stability |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023045166A Division JP2023088988A (ja) | 2017-03-03 | 2023-03-22 | 改善された安定性を有する製剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2020509095A JP2020509095A (ja) | 2020-03-26 |
| JP2020509095A5 true JP2020509095A5 (https=) | 2021-04-08 |
Family
ID=61692107
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019569659A Pending JP2020509095A (ja) | 2017-03-03 | 2018-03-02 | 改善された安定性を有する製剤 |
| JP2023045166A Pending JP2023088988A (ja) | 2017-03-03 | 2023-03-22 | 改善された安定性を有する製剤 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023045166A Pending JP2023088988A (ja) | 2017-03-03 | 2023-03-22 | 改善された安定性を有する製剤 |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US11629118B2 (https=) |
| EP (1) | EP3589280B1 (https=) |
| JP (2) | JP2020509095A (https=) |
| KR (2) | KR20240032149A (https=) |
| CN (2) | CN110494415A (https=) |
| AU (1) | AU2018226879B2 (https=) |
| CA (1) | CA3054948C (https=) |
| ES (1) | ES2975417T3 (https=) |
| MX (1) | MX394833B (https=) |
| WO (1) | WO2018161054A1 (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3589280B1 (en) * | 2017-03-03 | 2024-02-07 | Inspirna, Inc. | Formulations with improved stability |
| CA3078981A1 (en) | 2017-11-21 | 2019-05-31 | Rgenix, Inc. | Polymorphs and uses thereof |
| TWI888447B (zh) | 2019-12-13 | 2025-07-01 | 美商因思博納公司 | 金屬鹽及其用途 |
| CA3212583A1 (en) * | 2021-03-27 | 2022-10-06 | Daniel Gooding | Compositions having improved bioavailability of therapeutics |
| EP4493151A2 (en) * | 2022-03-14 | 2025-01-22 | TRX Biosciences Limited | Compositions having improved bioavailability of therapeutics and uses thereof |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2680749A (en) | 1951-12-01 | 1954-06-08 | Eastman Kodak Co | Water-soluble tocopherol derivatives |
| US3102078A (en) | 1961-01-13 | 1963-08-27 | Eastman Kodak Co | Water-dispersible vitamin preparations |
| US6340473B1 (en) | 1999-07-07 | 2002-01-22 | R.P. Scherer Technologies, Inc. | Film forming compositions comprising modified starches and iota-carrageenan and methods for manufacturing soft capsules using same |
| US6884060B2 (en) | 2001-11-02 | 2005-04-26 | R.P. Scherer Technologies, Inc. | Apparatus for manufacturing encapsulated products |
| EP1575495A4 (en) | 2002-03-27 | 2009-12-02 | Smithkline Beecham Corp | COMPOUNDS AND METHODS |
| EP1490047B1 (en) | 2002-03-27 | 2009-12-30 | SmithKline Beecham Corporation | Certain pharmaceutically useful substituted aminoalkyl heterocycles |
| US7560586B2 (en) | 2002-03-27 | 2009-07-14 | Smithkline Beecham Corporation | Acid and ester compounds and methods of using the same |
| AU2003220558A1 (en) | 2002-03-27 | 2004-06-03 | Smithkline Beecham Corporation | Amide compounds and methods of using the same |
| US20040219274A1 (en) | 2003-04-29 | 2004-11-04 | Cook Phillip Michael | Beverages containing water-soluble vitamin E |
| KR20070072888A (ko) * | 2004-10-25 | 2007-07-06 | 니뽄 다바코 산교 가부시키가이샤 | 용해성 및 안정성이 개선된 고형 제제 및 그의 제조 방법 |
| US8231896B2 (en) | 2004-11-08 | 2012-07-31 | R.P. Scherer Technologies, Llc | Non-gelatin soft capsule system |
| CN101232871A (zh) | 2005-08-03 | 2008-07-30 | 伊士曼化工公司 | 生育酚聚乙二醇琥珀酸酯粉末及其制备方法 |
| AU2013302861A1 (en) | 2012-08-13 | 2015-03-05 | The Rockefeller University | Treatment and diagnosis of melanoma |
| WO2015106164A1 (en) * | 2014-01-10 | 2015-07-16 | Rgenix, Inc. | Lxr agonists and uses thereof |
| US20190125745A1 (en) * | 2014-12-17 | 2019-05-02 | Rgenix, Inc. | Treatment and diagnosis of cancer |
| EP3589280B1 (en) * | 2017-03-03 | 2024-02-07 | Inspirna, Inc. | Formulations with improved stability |
-
2018
- 2018-03-02 EP EP18712347.6A patent/EP3589280B1/en active Active
- 2018-03-02 MX MX2019010330A patent/MX394833B/es unknown
- 2018-03-02 CN CN201880021207.3A patent/CN110494415A/zh active Pending
- 2018-03-02 KR KR1020247006055A patent/KR20240032149A/ko not_active Ceased
- 2018-03-02 CA CA3054948A patent/CA3054948C/en active Active
- 2018-03-02 WO PCT/US2018/020797 patent/WO2018161054A1/en not_active Ceased
- 2018-03-02 US US15/911,062 patent/US11629118B2/en active Active
- 2018-03-02 JP JP2019569659A patent/JP2020509095A/ja active Pending
- 2018-03-02 KR KR1020197029073A patent/KR102641778B1/ko active Active
- 2018-03-02 ES ES18712347T patent/ES2975417T3/es active Active
- 2018-03-02 CN CN202310918394.8A patent/CN117126069A/zh active Pending
- 2018-03-02 AU AU2018226879A patent/AU2018226879B2/en active Active
-
2023
- 2023-03-22 JP JP2023045166A patent/JP2023088988A/ja active Pending
-
2024
- 2024-07-18 US US18/777,110 patent/US20250188018A1/en active Pending
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