JP2019503354A5 - - Google Patents
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- Publication number
- JP2019503354A5 JP2019503354A5 JP2018532397A JP2018532397A JP2019503354A5 JP 2019503354 A5 JP2019503354 A5 JP 2019503354A5 JP 2018532397 A JP2018532397 A JP 2018532397A JP 2018532397 A JP2018532397 A JP 2018532397A JP 2019503354 A5 JP2019503354 A5 JP 2019503354A5
- Authority
- JP
- Japan
- Prior art keywords
- oil
- retinoic acid
- water emulsion
- analog
- emulsion
- 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
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 claims description 37
- 239000007764 o/w emulsion Substances 0.000 claims description 37
- 229930002330 retinoic acid Natural products 0.000 claims description 37
- 229960001727 tretinoin Drugs 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 15
- 239000000839 emulsion Substances 0.000 claims description 14
- 230000002163 immunogen Effects 0.000 claims description 13
- 239000003921 oil Substances 0.000 claims description 10
- 235000019198 oils Nutrition 0.000 claims description 10
- YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 claims description 7
- BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 claims description 7
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 claims description 7
- 229940031439 squalene Drugs 0.000 claims description 7
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 claims description 7
- 239000004094 surface-active agent Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 235000010384 tocopherol Nutrition 0.000 claims description 4
- 229960001295 tocopherol Drugs 0.000 claims description 4
- 229930003799 tocopherol Natural products 0.000 claims description 4
- 239000011732 tocopherol Substances 0.000 claims description 4
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 claims description 4
- 229950008882 polysorbate Drugs 0.000 claims description 3
- 229920000136 polysorbate Polymers 0.000 claims description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical group CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims description 2
- FLPJVCMIKUWSDR-UHFFFAOYSA-N 2-(4-formylphenoxy)acetamide Chemical compound NC(=O)COC1=CC=C(C=O)C=C1 FLPJVCMIKUWSDR-UHFFFAOYSA-N 0.000 claims description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 2
- 239000004322 Butylated hydroxytoluene Chemical group 0.000 claims description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical group CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 2
- 239000005642 Oleic acid Substances 0.000 claims description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 claims description 2
- 229940095259 butylated hydroxytoluene Drugs 0.000 claims description 2
- 229940074979 cetyl palmitate Drugs 0.000 claims description 2
- PXDJXZJSCPSGGI-UHFFFAOYSA-N hexadecanoic acid hexadecyl ester Natural products CCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC PXDJXZJSCPSGGI-UHFFFAOYSA-N 0.000 claims description 2
- 230000001571 immunoadjuvant effect Effects 0.000 claims description 2
- 239000000568 immunological adjuvant Substances 0.000 claims description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 2
- 239000000787 lecithin Chemical group 0.000 claims description 2
- 229940067606 lecithin Drugs 0.000 claims description 2
- 235000010445 lecithin Nutrition 0.000 claims description 2
- 239000002609 medium Chemical group 0.000 claims description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical group CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 2
- 229960002969 oleic acid Drugs 0.000 claims description 2
- 235000021313 oleic acid Nutrition 0.000 claims description 2
- 239000011148 porous material Substances 0.000 claims description 2
- 235000012424 soybean oil Nutrition 0.000 claims description 2
- 239000003549 soybean oil Substances 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- 150000003626 triacylglycerols Chemical class 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 230000028993 immune response Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP15202332 | 2015-12-23 | ||
| EP15202332.1 | 2015-12-23 | ||
| PCT/EP2016/082096 WO2017108902A1 (en) | 2015-12-23 | 2016-12-21 | Oil-in-water emulsions including retinoic acid |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019503354A JP2019503354A (ja) | 2019-02-07 |
| JP2019503354A5 true JP2019503354A5 (https=) | 2020-02-13 |
| JP6995756B2 JP6995756B2 (ja) | 2022-02-04 |
Family
ID=55085473
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018532397A Active JP6995756B2 (ja) | 2015-12-23 | 2016-12-21 | レチノイン酸を含む水中油型エマルジョン |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US11197826B2 (https=) |
| EP (1) | EP3393481A1 (https=) |
| JP (1) | JP6995756B2 (https=) |
| WO (1) | WO2017108902A1 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA3026108A1 (en) | 2016-06-10 | 2017-12-14 | Clarity Cosmetics Inc. | Non-comedogenic hair and scalp care formulations and method for use |
| US12233177B2 (en) | 2019-09-16 | 2025-02-25 | Amgen Inc. | Method for external sterilization of drug delivery device |
| CN113713093A (zh) * | 2021-08-31 | 2021-11-30 | 中国人民解放军陆军军医大学 | 一种新型高效增强体液免疫应答和粘膜免疫应答的维甲酸纳米乳佐剂及其制备方法和应用 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2090104C (en) | 1991-06-27 | 2002-05-28 | Charles E. Clum | Stabilized retinoid-containing skin care compositions |
| ATE179883T1 (de) | 1993-07-03 | 1999-05-15 | Procter & Gamble | Persönliches reinigungsmittel |
| US5855893A (en) * | 1997-02-14 | 1999-01-05 | Elizabeth Arden Co., Division Of Conopco, Inc. | Trichodesma lanicum seed extract as an anti-irritant in compositions containing hydroxy acids or retinoids |
| KR100258674B1 (ko) * | 1997-09-12 | 2000-07-01 | 서경배 | 안정성이 개선된 레티노이드를 함유하는 친수형 화장료의 제조방법 |
| TWI224107B (en) * | 1998-10-22 | 2004-11-21 | Pfizer Prod Inc | Novel proteins from actinobacillus pleuropneumoniae |
| US6531141B1 (en) * | 2000-03-07 | 2003-03-11 | Ortho-Mcneil Pharmaceutical, Inc. | Oil-in-water emulsion containing tretinoin |
| AU2010203223B9 (en) * | 2009-01-05 | 2015-10-08 | Epitogenesis Inc. | Adjuvant compositions and methods of use |
| EP2506832B1 (en) * | 2009-12-03 | 2014-02-26 | Novartis AG | Hydrophilic filtration during manufacture of vaccine adjuvants |
| FR2963241B1 (fr) * | 2010-07-30 | 2014-10-24 | Inst Rech Developpement Ird | Vaccin contre le paludisme gestationnel |
| US8986704B2 (en) * | 2012-07-06 | 2015-03-24 | Valneva Austria Gmbh | Mutant fragments of OspA and methods and uses relating thereto |
| US20180296663A1 (en) * | 2015-06-17 | 2018-10-18 | Curevac Ag | Vaccine composition |
-
2016
- 2016-12-21 EP EP16815858.2A patent/EP3393481A1/en active Pending
- 2016-12-21 US US16/065,468 patent/US11197826B2/en active Active
- 2016-12-21 WO PCT/EP2016/082096 patent/WO2017108902A1/en not_active Ceased
- 2016-12-21 JP JP2018532397A patent/JP6995756B2/ja active Active
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