JP2019517550A5 - - Google Patents
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- Publication number
- JP2019517550A5 JP2019517550A5 JP2018564301A JP2018564301A JP2019517550A5 JP 2019517550 A5 JP2019517550 A5 JP 2019517550A5 JP 2018564301 A JP2018564301 A JP 2018564301A JP 2018564301 A JP2018564301 A JP 2018564301A JP 2019517550 A5 JP2019517550 A5 JP 2019517550A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- multiple sclerosis
- deoxy
- dosage form
- oral dosage
- 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
- 239000006186 oral dosage form Substances 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 201000006417 multiple sclerosis Diseases 0.000 claims description 10
- 208000007118 chronic progressive multiple sclerosis Diseases 0.000 claims description 9
- ASLUCFFROXVMFL-UHFFFAOYSA-N andrographolide Natural products CC1(CO)C(O)CCC2(C)C(CC=C3/C(O)OCC3=O)C(=C)CCC12 ASLUCFFROXVMFL-UHFFFAOYSA-N 0.000 claims description 7
- WKKBRRFSRMDTJB-JYBIWHBTSA-N 4-[2-[(1R,4aS,5R,8aS)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethyl]-2H-furan-5-one Chemical compound C([C@H]1[C@]2(C)CCC[C@]([C@H]2CCC1=C)(CO)C)CC1=CCOC1=O WKKBRRFSRMDTJB-JYBIWHBTSA-N 0.000 claims description 6
- 238000003556 assay Methods 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- BOJKULTULYSRAS-OTESTREVSA-N Andrographolide Chemical compound C([C@H]1[C@]2(C)CC[C@@H](O)[C@]([C@H]2CCC1=C)(CO)C)\C=C1/[C@H](O)COC1=O BOJKULTULYSRAS-OTESTREVSA-N 0.000 claims description 5
- 206010053395 Progressive multiple sclerosis Diseases 0.000 claims description 5
- GELKGHVAFRCJNA-UHFFFAOYSA-N 2,2-Dimethyloxirane Chemical compound CC1(C)CO1 GELKGHVAFRCJNA-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 4
- BOJKULTULYSRAS-QPSYGYIJSA-N (3z,4s)-3-[2-[(1r,4as,5r,6r,8as)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1h-naphthalen-1-yl]ethylidene]-4-hydroxyoxolan-2-one Chemical compound C([C@H]1[C@]2(C)CC[C@@H](O)[C@]([C@H]2CCC1=C)(CO)C)\C=C1\[C@H](O)COC1=O BOJKULTULYSRAS-QPSYGYIJSA-N 0.000 claims description 3
- YIIRVUDGRKEWBV-UHFFFAOYSA-N (E)-3-(2-((1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydronaphthalen-1-yl)ethylidene)furan-2(3H)-one Natural products C=C1CCC2C(C)(CO)C(O)CCC2(C)C1CC=C1C=COC1=O YIIRVUDGRKEWBV-UHFFFAOYSA-N 0.000 claims description 3
- XMJAJFVLHDIEHF-CRBRZBHVSA-N 14-Deoxy-11,12-didehydroandrographolide Chemical compound C(/[C@@H]1C(=C)CC[C@H]2[C@@]1(C)CC[C@@H](O)[C@]2(CO)C)=C\C1=CCOC1=O XMJAJFVLHDIEHF-CRBRZBHVSA-N 0.000 claims description 3
- XMJAJFVLHDIEHF-UHFFFAOYSA-N 14-deoxy-11, 12-didehydroandrographolide Natural products OCC1(C)C(O)CCC2(C)C1CCC(=C)C2C=CC1=CCOC1=O XMJAJFVLHDIEHF-UHFFFAOYSA-N 0.000 claims description 3
- YIIRVUDGRKEWBV-YSDSKTICSA-N 14-deoxy-11,12-didehydroandrographolide Natural products C[C@@]1(CO)[C@H](O)CC[C@@]2(C)[C@H](CC=C/3C=COC3=O)C(=C)CC[C@H]12 YIIRVUDGRKEWBV-YSDSKTICSA-N 0.000 claims description 3
- BNLCOXWUZAOLDT-UHFFFAOYSA-N 14-deoxy-11-hydroxyandrographolide Natural products OCC1(C)C(O)CCC2(C)C1CCC(=C)C2C(O)CC1=CCOC1=O BNLCOXWUZAOLDT-UHFFFAOYSA-N 0.000 claims description 3
- SJKRRZPXYGTAGA-UHFFFAOYSA-N 14-deoxy-12-methoxyandrographolide Natural products C=C1CCC2C(C)(CO)C(O)CCC2(C)C1CC(OC)C1=CCOC1=O SJKRRZPXYGTAGA-UHFFFAOYSA-N 0.000 claims description 3
- KHQNSSJNIXVKMK-UHFFFAOYSA-N 14-deoxy-12R-hydroxyandrographolide Natural products C=C1CCC2C(C)(CO)C(O)CCC2(C)C1CC(O)C1=CCOC1=O KHQNSSJNIXVKMK-UHFFFAOYSA-N 0.000 claims description 3
- LMOGEODVJJLYGW-UHFFFAOYSA-N 14-deoxy-17beta-hydroxyandrographolide Natural products OCC1CCC2C(C)(CO)C(O)CCC2(C)C1CCC1=CCOC1=O LMOGEODVJJLYGW-UHFFFAOYSA-N 0.000 claims description 3
- GVRNTWSGBWPJGS-DSJDWBEOSA-N 14-deoxyandrographolide Natural products O=C1C(CC[C@@H]2C(=C)CC[C@@H]3[C@@](CO)(C)[C@H](O)CC[C@]23C)=CCO1 GVRNTWSGBWPJGS-DSJDWBEOSA-N 0.000 claims description 3
- WKKBRRFSRMDTJB-UHFFFAOYSA-N 19-hydroxy-labda 8(17),13-diene-15,16-olide Natural products C=C1CCC2C(C)(CO)CCCC2(C)C1CCC1=CCOC1=O WKKBRRFSRMDTJB-UHFFFAOYSA-N 0.000 claims description 3
- KHQNSSJNIXVKMK-UQZPWQSVSA-N 4-[(1r)-2-[(1r,4as,5r,6r,8as)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1h-naphthalen-1-yl]-1-hydroxyethyl]-2h-furan-5-one Chemical compound C1([C@H](O)C[C@H]2[C@]3(C)CC[C@@H](O)[C@]([C@H]3CCC2=C)(CO)C)=CCOC1=O KHQNSSJNIXVKMK-UQZPWQSVSA-N 0.000 claims description 3
- WQHWOZANSOUSAY-LZBAHHAZSA-N 4-[(e)-2-[(1r,4as,5r,6r,8ar)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1h-naphthalen-1-yl]ethenyl]-2-[2-[(1r,4as,5r,6r,8ar)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1h-naphthalen-1 Chemical compound C([C@H]1[C@]2(C)CC[C@@H](O)[C@]([C@H]2CCC1=C)(CO)C)C(C1C=C(\C=C\[C@H]2[C@@]3(CC[C@@H](O)[C@@](C)(CO)[C@H]3CCC2=C)C)C(=O)O1)C1=CCOC1=O WQHWOZANSOUSAY-LZBAHHAZSA-N 0.000 claims description 3
- LMOGEODVJJLYGW-UQZPWQSVSA-N 4-[2-[(1r,2s,4as,5r,6r,8as)-6-hydroxy-2,5-bis(hydroxymethyl)-5,8a-dimethyl-1,2,3,4,4a,6,7,8-octahydronaphthalen-1-yl]ethyl]-2h-furan-5-one Chemical compound C([C@H]1[C@]2(C)CC[C@@H](O)[C@]([C@H]2CC[C@@H]1CO)(CO)C)CC1=CCOC1=O LMOGEODVJJLYGW-UQZPWQSVSA-N 0.000 claims description 3
- GVRNTWSGBWPJGS-YSDSKTICSA-N 4-[2-[(1r,4as,5r,6r,8as)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1h-naphthalen-1-yl]ethyl]-2h-furan-5-one Chemical compound C([C@H]1[C@]2(C)CC[C@@H](O)[C@]([C@H]2CCC1=C)(CO)C)CC1=CCOC1=O GVRNTWSGBWPJGS-YSDSKTICSA-N 0.000 claims description 3
- YGCYRQKJYWQXHG-RDNQFMDVSA-N 4-[2-[(1r,4as,5r,8as)-5,8a-dimethyl-2-methylidene-5-[[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,4,4a,6,7,8-hexahydro-1h-naphthalen-1-yl]ethyl]-2h-furan-5-one Chemical compound C([C@@]1(C)[C@H]2CCC(=C)[C@@H](CCC=3C(OCC=3)=O)[C@]2(C)CCC1)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O YGCYRQKJYWQXHG-RDNQFMDVSA-N 0.000 claims description 3
- YQZCSRAURNLCEK-WZLKLWACSA-N 4-[2-[(1s,2r,4as,5r,6r,8ar)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethylspiro[3,4,4a,6,7,8-hexahydro-1h-naphthalene-2,2'-oxirane]-1-yl]ethyl]-2h-furan-5-one Chemical compound C([C@H]1[C@]2(C)CC[C@@H](O)[C@]([C@H]2CC[C@@]11OC1)(CO)C)CC1=CCOC1=O YQZCSRAURNLCEK-WZLKLWACSA-N 0.000 claims description 3
- YQZCSRAURNLCEK-UHFFFAOYSA-N 8,17-epoxy-14-deoxyandrographolide Natural products C1OC21CCC1C(C)(CO)C(O)CCC1(C)C2CCC1=CCOC1=O YQZCSRAURNLCEK-UHFFFAOYSA-N 0.000 claims description 3
- BOJKULTULYSRAS-BEUDANMRSA-N Andropanolide Natural products O=C1/C(=C/C[C@@H]2C(=C)CC[C@@H]3[C@@](CO)(C)[C@H](O)CC[C@]23C)/[C@H](O)CO1 BOJKULTULYSRAS-BEUDANMRSA-N 0.000 claims description 3
- WQHWOZANSOUSAY-UHFFFAOYSA-N Bisandrographolide A Natural products C=C1CCC2C(C)(CO)C(O)CCC2(C)C1CC(C1C=C(C=CC2C3(CCC(O)C(C)(CO)C3CCC2=C)C)C(=O)O1)C1=CCOC1=O WQHWOZANSOUSAY-UHFFFAOYSA-N 0.000 claims description 3
- 206010067063 Progressive relapsing multiple sclerosis Diseases 0.000 claims description 3
- 239000002131 composite material Substances 0.000 claims description 3
- XMJAJFVLHDIEHF-YSDSKTICSA-N dehydroandrographolide Natural products C([C@@H]1C(=C)CC[C@H]2[C@@]1(C)CC[C@@H](O)[C@]2(CO)C)=CC1=CCOC1=O XMJAJFVLHDIEHF-YSDSKTICSA-N 0.000 claims description 3
- MEEPUSVTMHGIPC-UHFFFAOYSA-N deoxyandrographiside Natural products OC1CCC2(C)C(CCC=3C(OCC=3)=O)C(=C)CCC2C1(C)COC1OC(CO)C(O)C(O)C1O MEEPUSVTMHGIPC-UHFFFAOYSA-N 0.000 claims description 3
- GVRNTWSGBWPJGS-UHFFFAOYSA-N deoxyandrographolide Natural products C=C1CCC2C(C)(CO)C(O)CCC2(C)C1CCC1=CCOC1=O GVRNTWSGBWPJGS-UHFFFAOYSA-N 0.000 claims description 3
- 230000005021 gait Effects 0.000 claims description 3
- BBGWVUQBIGGVLS-UHFFFAOYSA-N neoandrographolide Natural products CC1(COC2OC(CO)C(O)C(O)C2O)C(O)CCC3(C)C(CCC4=C(O)COC4=O)C(=C)CCC13 BBGWVUQBIGGVLS-UHFFFAOYSA-N 0.000 claims description 3
- YGCYRQKJYWQXHG-UHFFFAOYSA-N neoandrographoside Natural products C1CCC2(C)C(CCC=3C(OCC=3)=O)C(=C)CCC2C1(C)COC1OC(CO)C(O)C(O)C1O YGCYRQKJYWQXHG-UHFFFAOYSA-N 0.000 claims description 3
- 206010063401 primary progressive multiple sclerosis Diseases 0.000 claims description 3
- 230000000750 progressive effect Effects 0.000 claims description 3
- 201000008628 secondary progressive multiple sclerosis Diseases 0.000 claims description 3
- 102000014150 Interferons Human genes 0.000 claims description 2
- 108010050904 Interferons Proteins 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000000837 carbohydrate group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000000539 dimer Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 229940079322 interferon Drugs 0.000 claims description 2
- 239000000178 monomer Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 238000000034 method Methods 0.000 description 4
- 230000001413 cellular effect Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2021113384A JP2021165304A (ja) | 2016-06-08 | 2021-07-08 | アンドログラホリドが進化型の多発性硬化症を処置する |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662347218P | 2016-06-08 | 2016-06-08 | |
| US62/347,218 | 2016-06-08 | ||
| PCT/US2017/036463 WO2017214346A1 (en) | 2016-06-08 | 2017-06-08 | Andrographolide treats progressive forms of multiple sclerosis |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021113384A Division JP2021165304A (ja) | 2016-06-08 | 2021-07-08 | アンドログラホリドが進化型の多発性硬化症を処置する |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019517550A JP2019517550A (ja) | 2019-06-24 |
| JP2019517550A5 true JP2019517550A5 (enExample) | 2020-07-09 |
| JP6928963B2 JP6928963B2 (ja) | 2021-09-01 |
Family
ID=60578163
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018564301A Active JP6928963B2 (ja) | 2016-06-08 | 2017-06-08 | アンドログラホリドが進化型の多発性硬化症を処置する |
| JP2021113384A Pending JP2021165304A (ja) | 2016-06-08 | 2021-07-08 | アンドログラホリドが進化型の多発性硬化症を処置する |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021113384A Pending JP2021165304A (ja) | 2016-06-08 | 2021-07-08 | アンドログラホリドが進化型の多発性硬化症を処置する |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US10722492B2 (enExample) |
| EP (1) | EP3468553B1 (enExample) |
| JP (2) | JP6928963B2 (enExample) |
| CN (1) | CN109562097B (enExample) |
| CA (1) | CA3026770C (enExample) |
| DK (1) | DK3468553T3 (enExample) |
| MX (1) | MX386393B (enExample) |
| WO (1) | WO2017214346A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019126759A1 (en) * | 2017-12-22 | 2019-06-27 | Convelo Therapeutics, Inc. | Compounds and methods of promoting myelination |
| CN109293607A (zh) * | 2018-11-14 | 2019-02-01 | 株洲千金药业股份有限公司 | 一种具有抗炎作用的化合物及其在制备抗炎药物中的应用 |
| CN109223770A (zh) * | 2018-11-14 | 2019-01-18 | 株洲千金药业股份有限公司 | 一种具有镇痛作用的化合物及其在制备镇痛药物中的应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003059387A2 (en) * | 2001-12-21 | 2003-07-24 | Ilex Oncology, Inc. | Combination comprising anti-cd52 antibodies and other therapeutic agents for treatment for multiple sclerosis |
| KR20070026398A (ko) * | 2004-02-03 | 2007-03-08 | 우니베르시다드 오스뜨랄 데 칠레 | Ｐｐａｒ-감마 수용체의 활성화에 의한 자가면역 질환 및알츠하이머병의 치료에 유용한, 천심련으로부터 추출된랍단 디테르펜을 포함하는 조성물 |
| JP5936707B2 (ja) * | 2011-12-21 | 2016-06-22 | イノバイオサイエンス， エルエルシー | インターフェロンおよびアンドログラホリドを用いた多発性硬化症のための併用療法 |
-
2017
- 2017-06-08 JP JP2018564301A patent/JP6928963B2/ja active Active
- 2017-06-08 WO PCT/US2017/036463 patent/WO2017214346A1/en not_active Ceased
- 2017-06-08 DK DK17810987.2T patent/DK3468553T3/da active
- 2017-06-08 MX MX2018015208A patent/MX386393B/es unknown
- 2017-06-08 CN CN201780035899.2A patent/CN109562097B/zh active Active
- 2017-06-08 EP EP17810987.2A patent/EP3468553B1/en active Active
- 2017-06-08 US US15/774,604 patent/US10722492B2/en active Active
- 2017-06-08 CA CA3026770A patent/CA3026770C/en active Active
-
2021
- 2021-07-08 JP JP2021113384A patent/JP2021165304A/ja active Pending
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