JPWO2017122495A1 - セラミド含量増加剤 - Google Patents
セラミド含量増加剤 Download PDFInfo
- Publication number
- JPWO2017122495A1 JPWO2017122495A1 JP2017561557A JP2017561557A JPWO2017122495A1 JP WO2017122495 A1 JPWO2017122495 A1 JP WO2017122495A1 JP 2017561557 A JP2017561557 A JP 2017561557A JP 2017561557 A JP2017561557 A JP 2017561557A JP WO2017122495 A1 JPWO2017122495 A1 JP WO2017122495A1
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- ceramide
- formula
- hydrogen atom
- compound represented
- 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
- 229940106189 ceramide Drugs 0.000 title claims abstract description 126
- YDNKGFDKKRUKPY-JHOUSYSJSA-N C16 ceramide Natural products CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)C=CCCCCCCCCCCCCC YDNKGFDKKRUKPY-JHOUSYSJSA-N 0.000 title claims abstract description 123
- CRJGESKKUOMBCT-VQTJNVASSA-N N-acetylsphinganine Chemical compound CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(C)=O CRJGESKKUOMBCT-VQTJNVASSA-N 0.000 title claims abstract description 123
- ZVEQCJWYRWKARO-UHFFFAOYSA-N ceramide Natural products CCCCCCCCCCCCCCC(O)C(=O)NC(CO)C(O)C=CCCC=C(C)CCCCCCCCC ZVEQCJWYRWKARO-UHFFFAOYSA-N 0.000 title claims abstract description 123
- VVGIYYKRAMHVLU-UHFFFAOYSA-N newbouldiamide Natural products CCCCCCCCCCCCCCCCCCCC(O)C(O)C(O)C(CO)NC(=O)CCCCCCCCCCCCCCCCC VVGIYYKRAMHVLU-UHFFFAOYSA-N 0.000 title claims abstract description 123
- 150000001875 compounds Chemical class 0.000 claims abstract description 121
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 40
- 150000003839 salts Chemical class 0.000 claims abstract description 39
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 39
- 229940125532 enzyme inhibitor Drugs 0.000 claims abstract description 31
- 239000002532 enzyme inhibitor Substances 0.000 claims abstract description 31
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 28
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 68
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- 125000002252 acyl group Chemical group 0.000 claims description 28
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- 238000000034 method Methods 0.000 claims description 26
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
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- 125000003302 alkenyloxy group Chemical group 0.000 claims description 5
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- 235000002639 sodium chloride Nutrition 0.000 description 29
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- 125000003545 alkoxy group Chemical group 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
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- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 9
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- 239000000284 extract Substances 0.000 description 7
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 7
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- 230000029663 wound healing Effects 0.000 description 7
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- 208000027418 Wounds and injury Diseases 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 6
- 229920002674 hyaluronan Polymers 0.000 description 6
- 229960003160 hyaluronic acid Drugs 0.000 description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 6
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- 210000000434 stratum corneum Anatomy 0.000 description 6
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- 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 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 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 description 5
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
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Abstract
Description
〔1〕 式(I)で表される化合物又はその医薬上許容される塩からなる、セラミド含量増加剤。
R2はそれぞれ独立して、水素原子、置換されていてもよいアルキル、置換されていてもよいアルケニル、置換されていてもよいアルキニル、置換されていてもよいシクロアルキル、置換されていてもよいシクロアルケニル、置換されていてもよいアリール、置換されていてもよいヘテロアリール、又は置換されていてもよいアシルであり;
R3は水素原子、−CH2OR4、−CHOR4−CH2OR4、もしくは−COOR4であり、ここでR4は水素原子、置換されていてもよいアルキル、置換されていてもよいアルケニル、置換されていてもよいアルキニル、置換されていてもよいシクロアルキル、置換されていてもよいシクロアルケニル、置換されていてもよいアリール、置換されていてもよいヘテロアリール、又は置換されていてもよいアシルであり;
nは0又は1である)
〔2〕 前記式(I)で表される化合物又はその医薬上許容される塩からなる、セラミド分解酵素阻害剤。
〔3〕 式(II)で表される化合物又はその医薬上許容される塩を含む、セラミド合成促進剤。
〔4〕 前記〔1〕記載のセラミド含量増加剤、前記〔2〕記載のセラミド分解酵素阻害剤、又は、前記〔3〕記載のセラミド合成促進剤を含有してなる組成物。
〔5〕 下記式で表される化合物。
〔7〕 前記〔2〕に記載の式(I)で表される化合物、前記〔3〕に記載の式(II)で表される化合物、又はそれらの医薬上許容される塩の有効量を、下記(i)〜(iii)から選ばれるいずれかの予防又は改善を必要とする個体に投与する工程を含む、下記(i)〜(iii)から選ばれるいずれかを予防及び/又は改善する方法。
(i) アトピー性皮膚炎又はアトピー性皮膚炎が起因となる疾患の症状
(ii) 皮脂欠乏症又は皮脂欠乏症が起因となる疾患の症状
(iii) 創傷
〔8〕 細胞におけるセラミド量を増加するための、前記〔2〕に記載の式(I)で表される化合物、前記〔3〕に記載の式(II)で表される化合物、又はそれらの医薬上許容される塩。
〔9〕 下記(i)〜(iii)から選ばれるいずれかを予防及び/又は改善するための、前記〔2〕に記載の式(I)で表される化合物、前記〔3〕に記載の式(II)で表される化合物、又はそれらの医薬上許容される塩。
(i) アトピー性皮膚炎又はアトピー性皮膚炎が起因となる疾患の症状
(ii) 皮脂欠乏症又は皮脂欠乏症が起因となる疾患の症状
(iii) 創傷
〔10〕 細胞におけるセラミド量を増加するための、前記〔2〕に記載の式(I)で表される化合物、前記〔3〕に記載の式(II)で表される化合物、又はそれらの医薬上許容される塩の使用。
〔11〕 下記(i)〜(iii)から選ばれるいずれかを予防及び/又は改善するための、前記〔2〕に記載の式(I)で表される化合物、前記〔3〕に記載の式(II)で表される化合物、又はそれらの医薬上許容される塩の使用。
(i) アトピー性皮膚炎又はアトピー性皮膚炎が起因となる疾患の症状
(ii) 皮脂欠乏症又は皮脂欠乏症が起因となる疾患の症状
(iii) 創傷
〔12〕 細胞におけるセラミド量を増加するための組成物の調製における、前記〔2〕に記載の式(I)で表される化合物、前記〔3〕に記載の式(II)で表される化合物、又はそれらの医薬上許容される塩の使用。
〔13〕 下記(i)〜(iii)から選ばれるいずれかを予防及び/又は改善するための組成物の調製における、前記〔2〕に記載の式(I)で表される化合物、前記〔3〕に記載の式(II)で表される化合物、又はそれらの医薬上許容される塩の使用。
(i) アトピー性皮膚炎又はアトピー性皮膚炎が起因となる疾患の症状
(ii) 皮脂欠乏症又は皮脂欠乏症が起因となる疾患の症状
(iii) 創傷
本発明のセラミド分解酵素阻害剤は、前記式(I)で示される5員環又は6員環の糖を基本骨格とする誘導体であることを特徴とする。なお、式(I)で表される化合物及びその医薬上許容される塩のことを、まとめて本発明の態様1の化合物と記載することもある。
1,5−anhydroglucitol, 1,4−anhydroglucitol, 1,5−anhydrogalactitol, 1,4−anhydrogalactitol, 1,4−anhydro−L−arabinitol, 1,4−anhydro−D−arabinitol, 1,5−anhydroxylitol, 1,4−anhydroxylitol, 1−deoxycellobiose, 1−deoxymaltose, 1−deoxylactose, trehalose, arbutin, salicin, phlorhizin, aesculin, apiin, daidzin, quercitrin, rutin, hesperidin, naringin, ruberythric acid, indicant, digitoxin, digitonin, 2,6−anhydro−L−gulonic acid, glucuronic acid, galacturonic acid, gluconolactone, baicalin, glycyrrhizin, 6−octanoyl−1,5−anhydroglucitol, n−octyl−β−D−glucopyranoside, hyaluronic acid, 6−carboxymetyl−1,5−anhydroglucitol, 2,3,4,6−tetraacetyl−1,5−anhydroglucitol, penta−O−acetyl−β−D−glucoside, penta−O−acetyl−α−D−glucoside, penta−O−acetyl−α−D−galactoside, α−D−cellobiose octaacetate, tetraacetyl ribofuranoside, neohesperidin, carminic acid, N−acetylneuraminic acid, 3,4,6−triacetyl−2−deoxy−D−glucose, 1,2,3,4−tetraacetyl−α−L−fucopyranoside, Neu5Ac α(2−3)Gal β(1−4)GlcNAc−β−pNP, methyl 1,2,3,4−tetra−O−acetyl−β−D−glucuronate, 2,3,4−tri−O−acetyl−1,5−anhydroglucuronic acid methylester, 1−deoxyglucuronic acid methylester, pentagalloylglucose, casuarictin, tellimagrandin I, tellimagrandin II, coriariin A, punicalagin, alienanin B, melasquanin A, melasquanin B, melasquanin C, melasquanin D, castamollinin, anogeissinin A, anogeissinin B, agrimoniin, rugosin A, strictinin, 2−galloyl−1,5−anhydroglucitol, 3−galloyl−1,5−anhydroglucitol, 4−galloyl−1,5−anhydroglucitol, 6−galloyl−1,5−anhydroglucitol, 2,3−digalloyl−1,5−anhydroglucitol, 2,4−digalloyl−1,5−anhydroglucitol, 2,6−digalloyl−1,5−anhydroglucitol, 3,6−digalloyl−1,5−anhydroglucitol, 4,6−digalloyl−1,5−anhydroglucitol, 2,3,6−trigalloyl−1,5−anhydroglucitol, 2,4,6−trigalloyl−1,5−anhydroglucitol, 2,3,4,6−tetragalloyl−1,5−anhydroglucitol
hyaluronic acid sodium salt, hyaluronic acid potassium salt, hyaluronic acid calcium salt, hyaluronic acid ammonium salt
本発明のセラミド合成促進剤は、前記式(II)で示されるように、6員環の糖(1,5-アンヒドロ-D-グルシトール、以降、「1,5-AG」と記載する場合もある)を基本骨格とし、少なくとも1個の水酸基に没食子酸のカルボキシル基がエステル結合した化合物であることを特徴とする。以降、式(II)で表される化合物及びその医薬上許容される塩のことを、まとめて本発明の態様2の化合物と記載することもある。なお、本明細書における用語「基」又は「置換基」は1価基を意味し、置換基の説明において、「基」なる用語を省略する場合もある。
〔下記(2)〕
[α]D 25: +15.3°(c1.0, chloroform); m.p. : 162-164 ℃;
1H NMR (CDCl3, 300 MHz) : δ3.30 (t, 1H), 3.72 (m, 3H), 4.04-4.15 (m, 3H), 4.56-4.81 (m, 5H), 5.03-5.11 (m, 13H), 5.32 (t, 1H), 7.23-7.43 (m, 44H);
13C NMR (CDCl3, 75 MHz) : δ 63.5, 68.3, 71.1, 71.3, 73.5, 75.1, 78.2, 83.0, 109.2, 109.5, 124.6, 124.8, 127.5, 127.6, 127.9, 128.1, 128.2, 128.5, 136.6, 136.8, 137.4, 137.5, 137.9;
IR (KBr) 465, 588, 696, 750, 860, 912, 977, 1027, 1120, 1203, 1338, 1373, 1427, 1500, 1589, 1720, 1810, 1880, 1953, 2867, 2938, 3031, 3064 cm-1.
〔下記(3)〕
[α]D 25: +63.4°(c1.0, methanol);
1H NMR (CD3OD, 300 MHz) : δ3.57-3.59(m, 2H), 3.66-3.72 (m, 1H), 3.94 (dd, 1H), 4.10 (dd, 1H), 4.34 (d, 1H), 5.03 (m, 1H), 7.01-7.20 (m, 4H);
13C NMR (CD3OD, 75 MHz) : δ 64.2, 71.0, 71.5, 72.6, 77.7, 78.2, 110.3, 110.4, 121.2, 121.3, 129.2, 129. 9, 139.9, 140.0, 146.4, 167.6, 168.1;
IR (KBr) 526, 565, 607, 661, 763, 811, 867, 997, 1037, 1099, 1240, 1348, 1452, 1540, 1616, 1700, 3396 cm-1;
ESI-TOFMS m/z : calcd for 491.08016; found, 491.07917.
Bligh, E. G., Dyer, W. J. (1959) A rapid method of total lipid extraction and purification. Can. J. Biochem. Physiol, 37, 911-917に記載の方法に従って、下記に示す化合物を合成した。
13C NMR (CD3OD, 75 MHz) : δ55.1, 67.2, 70.4, 71.1, 72.5, 74.0, 99.4, 111.2, 111.3, 122.0, 139.8, 147.5, 147.6, 169.4.
各化合物のin vitroセラミド分解酵素阻害活性を測定した。なお、上記製造例1で製造したサンプル以外は、市販品や公知の方法に従って合成したものを用いた。
各化合物によるin vivoのセラミド量増加を測定した。
3.0cm×3.0cm四方のSEKISUI シュープリームテープE(基材ポリプロピレン、アクリル系粘着剤)を軽く押し当てた後はがす操作を5回行い、各部位において5枚のテープを採取する。
得られたテープ5枚をメタノール90mL及びクロロホルム10mLの混合溶液に浸け、超音波を用いて約20分間抽出した後、メンブランフィルター(5μm)を通し、得られた溶液を25℃以下にて溶媒を留去する。得られた残差を真空ポンプを用いて乾燥させた後、これにクロロホルム/メタノール=99.5/0.5(v/v)溶液100mLを加えて溶解し、次いでwaters社製 Sep-Pak(登録商標)Vac RC(500mg)に通液する。得られたSep-Pak(登録商標)カートリッジにクロロホルム/メタノール=99.5/0.5(v/v)溶液60mLを通液した後、クロロホルム/メタノール=95/5(v/v)溶液60mLを通液する。クロロホルム/メタノール=95/5(v/v)溶液60mLを通液したフラクションを25℃以下で減圧濃縮した後、残差にクロロホルム/メタノール=9/1(v/v)0.5mLを加えて均一に溶解したものをサンプルとする。
各サンプル(A、B、C、D)それぞれ20μL及びセラミド標準品としてMatoreya社製 N-Tetracosanoyl-D-erythro-sphingosine(5mg/10mLクロロホルム溶液)10μLを、薄層クロマトグラフ板としてメルク社製薄層クロマトグラフ板(TLC Silica gel 60F254 ガラスプレート)、移動相としてクロロホルム/メタノール/酢酸=190/10/1(v/v/v)を用いて展開した後、8%硫酸銅水溶液、10%リン酸水溶液を順次噴霧した後、160℃で15分間加熱する。得られたスポットをImageJを用いて分析し、未塗布部位Dの発色を1とした場合の塗布部位A、B、Cの相対値を算出し、サンプル塗布による皮膚セラミド量の増加度合いを分析する。
各化合物のin vitroセラミド合成量を測定した。なお、上記製造例1及び2で製造したサンプル以外は、市販品や公知の方法に従って合成したものを用いた。
6-galloyl-1,5-anhydro-D-glucitolによる創傷治癒効果を評価した。
Claims (36)
- 式(I)で表される化合物又はその医薬上許容される塩からなる、セラミド含量増加剤。
R2はそれぞれ独立して、水素原子、置換されていてもよいアルキル、置換されていてもよいアルケニル、置換されていてもよいアルキニル、置換されていてもよいシクロアルキル、置換されていてもよいシクロアルケニル、置換されていてもよいアリール、置換されていてもよいヘテロアリール、又は置換されていてもよいアシルであり;
R3は水素原子、−CH2OR4、−CHOR4−CH2OR4、もしくは−COOR4であり、ここでR4は水素原子、置換されていてもよいアルキル、置換されていてもよいアルケニル、置換されていてもよいアルキニル、置換されていてもよいシクロアルキル、置換されていてもよいシクロアルケニル、置換されていてもよいアリール、置換されていてもよいヘテロアリール、又は置換されていてもよいアシルであり;
nは0又は1である) - 式(I)で表される化合物又はその医薬上許容される塩からなる、セラミド分解酵素阻害剤。
R2はそれぞれ独立して、水素原子、置換されていてもよいアルキル、置換されていてもよいアルケニル、置換されていてもよいアルキニル、置換されていてもよいシクロアルキル、置換されていてもよいシクロアルケニル、置換されていてもよいアリール、置換されていてもよいヘテロアリール、又は置換されていてもよいアシルであり;
R3は水素原子、−CH2OR4、−CHOR4−CH2OR4、もしくは−COOR4であり、ここでR4は水素原子、置換されていてもよいアルキル、置換されていてもよいアルケニル、置換されていてもよいアルキニル、置換されていてもよいシクロアルキル、置換されていてもよいシクロアルケニル、置換されていてもよいアリール、置換されていてもよいヘテロアリール、又は置換されていてもよいアシルであり;
nは0又は1である) - R2とR3から選ばれる少なくとも1つが、置換されていてもよいアシルを含む、請求項2記載のセラミド分解酵素阻害剤。
- R1がいずれも水素原子であり、かつ、R3が−COOR4であり、但し、R4は水素原子又は置換されていてもよいアルキルである、請求項2記載のセラミド分解酵素阻害剤。
- R1の一方が水素原子、他方がヒドロキシであり、かつ、R3が−COOR4であり、但し、R4は水素原子又は置換されていてもよいアルキルである、請求項2記載のセラミド分解酵素阻害剤。
- R1の一方が水素原子、他方が置換されていてもよいアルキルオキシであり、かつ、R3が−COOR4であり、但し、R4は水素原子又は置換されていてもよいアルキルである、請求項2記載のセラミド分解酵素阻害剤。
- 2個のR1が=Oを形成し、かつ、R3が−CH2OHである、請求項2記載のセラミド分解酵素阻害剤。
- 2個のR1が=Oを形成し、R3が−CH2OHであり、n=0である、請求項2記載のセラミド分解酵素阻害剤。
- 2個のR1が=Oを形成し、R3が−CH2OR4又は−CHOR4−CH2OR4であり、但し、R4は水素原子又は置換されていてもよいアシルである、請求項2記載のセラミド分解酵素阻害剤。
- R1がいずれも水素原子であり、かつ、R2のうち少なくとも一つが置換されていてもよいアシルである、請求項2記載のセラミド分解酵素阻害剤。
- R1の一方が水素原子、他方が置換されていてもよいアシルオキシであり、かつ、R2のうち少なくとも一つが置換されていてもよいアシルである、請求項2記載のセラミド分解酵素阻害剤。
- R1の一方が水素原子、他方が置換されていてもよいアシルオキシであり、R2のうち少なくとも一つが置換されていてもよいアシルであり、かつ、R3が−CH2OR4であり、但し、R4は水素原子又は置換されていてもよいアルキルである、請求項2記載のセラミド分解酵素阻害剤。
- R1がいずれも水素原子であり、R2がいずれも水素原子であり、かつ、R3が−CH2OR4又は−CHOR4−CH2OR4であり、但し、R4は置換されていてもよいアシルである、請求項2記載のセラミド分解酵素阻害剤。
- R1の一方が水素原子、他方が置換されていてもよいアルキルオキシであり、かつ、R3が−CH2OR4であり、但し、R4は水素原子又は置換されていてもよいアルキルである、請求項2記載のセラミド分解酵素阻害剤。
- R1がいずれも水素原子であり、R2がいずれも水素原子であり、かつ、R3が−CH2OR4又は−CHOR4−CH2OR4であり、但し、R4は水素原子である、請求項2記載のセラミド分解酵素阻害剤。
- 式(I)で表される化合物が、下記式で表される化合物である、請求項2記載のセラミド分解酵素阻害剤。
- 式(II)で表される化合物又はその医薬上許容される塩を含む、セラミド合成促進剤。
- R9がガロイル基である、請求項17記載のセラミド合成促進剤。
- R7及びR9は同時にガロイル基ではない、請求項17記載のセラミド合成促進剤。
- 式(II)で表される化合物が下記式で表される化合物である、請求項17又は18記載のセラミド合成促進剤。
- 式(II)で表される化合物が下記式で表される化合物である、請求項17又は18記載のセラミド合成促進剤。
- 式(II)で表される化合物が下記式で表される化合物である、請求項17又は18記載のセラミド合成促進剤。
- 式(II)で表される化合物が下記式で表される化合物である、請求項17又は18記載のセラミド合成促進剤。
- 請求項1記載のセラミド含量増加剤、請求項2〜16いずれか記載のセラミド分解酵素阻害剤、又は、請求項17〜23いずれか記載のセラミド合成促進剤を含有してなる組成物。
- 内服剤組成物、又は、外用剤組成物である、請求項24記載の組成物。
- セラミド量の低下が原因となる疾患の症状を改善又は治療するために用いられる、請求項24又は25記載の組成物。
- 下記(i)〜(iii)から選ばれるいずれかを改善又は治療するために用いられる、請求項26記載の組成物。
(i) アトピー性皮膚炎又はアトピー性皮膚炎が起因となる疾患の症状
(ii) 皮脂欠乏症又は皮脂欠乏症が起因となる疾患の症状
(iii) 創傷 - 下記式で表される化合物。
- 請求項2に記載の式(I)で表される化合物、請求項17に記載の式(II)で表される化合物、又はそれらの医薬上許容される塩の有効量を、細胞内セラミド量の増加を必要とする個体に投与する工程を含む、細胞内セラミド量の増加方法。
- 請求項2に記載の式(I)で表される化合物、請求項17に記載の式(II)で表される化合物、又はそれらの医薬上許容される塩の有効量を、下記(i)〜(iii)から選ばれるいずれかの予防又は改善を必要とする個体に投与する工程を含む、下記(i)〜(iii)から選ばれるいずれかを予防及び/又は改善する方法。
(i) アトピー性皮膚炎又はアトピー性皮膚炎が起因となる疾患の症状
(ii) 皮脂欠乏症又は皮脂欠乏症が起因となる疾患の症状
(iii) 創傷 - 細胞におけるセラミド量を増加するための、請求項2に記載の式(I)で表される化合物、請求項17に記載の式(II)で表される化合物、又はそれらの医薬上許容される塩。
- 下記(i)〜(iii)から選ばれるいずれかを予防及び/又は改善するための、請求項2に記載の式(I)で表される化合物、請求項17に記載の式(II)で表される化合物、又はそれらの医薬上許容される塩。
(i) アトピー性皮膚炎又はアトピー性皮膚炎が起因となる疾患の症状
(ii) 皮脂欠乏症又は皮脂欠乏症が起因となる疾患の症状
(iii) 創傷 - 細胞におけるセラミド量を増加するための、請求項2に記載の式(I)で表される化合物、請求項17に記載の式(II)で表される化合物、又はそれらの医薬上許容される塩の使用。
- 下記(i)〜(iii)から選ばれるいずれかを予防及び/又は改善するための、請求項2に記載の式(I)で表される化合物、請求項17に記載の式(II)で表される化合物、又はそれらの医薬上許容される塩の使用。
(i) アトピー性皮膚炎又はアトピー性皮膚炎が起因となる疾患の症状
(ii) 皮脂欠乏症又は皮脂欠乏症が起因となる疾患の症状
(iii) 創傷 - 細胞におけるセラミド量を増加するための組成物の調製における、請求項2に記載の式(I)で表される化合物、請求項17に記載の式(II)で表される化合物、又はそれらの医薬上許容される塩の使用。
- 下記(i)〜(iii)から選ばれるいずれかを予防及び/又は改善するための組成物の調製における、請求項2に記載の式(I)で表される化合物、請求項17に記載の式(II)で表される化合物、又はそれらの医薬上許容される塩の使用。
(i) アトピー性皮膚炎又はアトピー性皮膚炎が起因となる疾患の症状
(ii) 皮脂欠乏症又は皮脂欠乏症が起因となる疾患の症状
(iii) 創傷
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