JP4953627B2 - アラキドン酸代謝抑制剤 - Google Patents
アラキドン酸代謝抑制剤 Download PDFInfo
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- JP4953627B2 JP4953627B2 JP2005372505A JP2005372505A JP4953627B2 JP 4953627 B2 JP4953627 B2 JP 4953627B2 JP 2005372505 A JP2005372505 A JP 2005372505A JP 2005372505 A JP2005372505 A JP 2005372505A JP 4953627 B2 JP4953627 B2 JP 4953627B2
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- Prior art keywords
- arachidonic acid
- acid metabolism
- metabolism inhibitor
- present
- agent
- 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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- 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 title claims description 103
- 229940114079 arachidonic acid Drugs 0.000 title claims description 51
- 235000021342 arachidonic acid Nutrition 0.000 title claims description 51
- 230000004060 metabolic process Effects 0.000 title claims description 46
- 239000003112 inhibitor Substances 0.000 title claims description 41
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 230000017531 blood circulation Effects 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 8
- KVWWIYGFBYDJQC-UHFFFAOYSA-N methyl dihydrojasmonate Chemical group CCCCCC1C(CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-UHFFFAOYSA-N 0.000 claims description 8
- IPWBXORAIBJDDQ-UHFFFAOYSA-N methyl 2-hexyl-3-oxocyclopentane-1-carboxylate Chemical compound CCCCCCC1C(C(=O)OC)CCC1=O IPWBXORAIBJDDQ-UHFFFAOYSA-N 0.000 claims description 5
- 239000003146 anticoagulant agent Substances 0.000 claims description 4
- 229960004676 antithrombotic agent Drugs 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 3
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
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- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 4
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- PJVXUVWGSCCGHT-ZPYZYFCMSA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal;(3s,4r,5r)-1,3,4,5,6-pentahydroxyhexan-2-one Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O.OC[C@@H](O)[C@@H](O)[C@H](O)C(=O)CO PJVXUVWGSCCGHT-ZPYZYFCMSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound 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 description 1
- PQDRWMYDXMMMBP-UHFFFAOYSA-N 2-oxoicosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCC(=O)C(O)=O PQDRWMYDXMMMBP-UHFFFAOYSA-N 0.000 description 1
- MIDXCONKKJTLDX-UHFFFAOYSA-N 3,5-dimethylcyclopentane-1,2-dione Chemical compound CC1CC(C)C(=O)C1=O MIDXCONKKJTLDX-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- BAMZQDVORMCDEA-UHFFFAOYSA-N 5-oxoicosanoic acid Chemical compound CCCCCCCCCCCCCCCC(=O)CCCC(O)=O BAMZQDVORMCDEA-UHFFFAOYSA-N 0.000 description 1
- WBZFUFAFFUEMEI-UHFFFAOYSA-M Acesulfame k Chemical compound [K+].CC1=CC(=O)[N-]S(=O)(=O)O1 WBZFUFAFFUEMEI-UHFFFAOYSA-M 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 1
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- 206010012442 Dermatitis contact Diseases 0.000 description 1
- 239000004278 EU approved seasoning Substances 0.000 description 1
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- 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 1
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- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 239000004376 Sucralose Substances 0.000 description 1
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- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 239000003925 fat Substances 0.000 description 1
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- 235000019634 flavors Nutrition 0.000 description 1
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- 238000009434 installation Methods 0.000 description 1
- 239000007951 isotonicity adjuster Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 229940069445 licorice extract Drugs 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
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Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Cosmetics (AREA)
Description
で示される化合物としては、メチルジヒドロジャスモネートが香料化合物として市販されており、容易に入手することができる。本発明では、市販されているメチルジヒドロジャスモネートをそのまま使用してもよく、公知の方法により合成することもできる。また、公知の方法でエステル交換により、一般式のR部分をエチル基またはプロピル基に変換することもできる。また、市販のメチルジヒドロジャスモネートを加水分解してジヒドロジャスモネートとして使用することもできる。
人の血液に10%濃度になるように3.8%クエン酸ナトリウム液を加え、この血液を1000rpmで10分間遠心分離し、上層部を採取、これを多血小板血漿(PRP)とした。更に下層部を3000rpmで15分間遠心分離し、上層部より乏血小板血漿(PPP)を採取して、これを血小板凝集能測定時におけるコントロールとした。
(血小板凝集阻害率計算法)
PRP+凝集惹起剤のみを加えたときの最大凝集率をAとする。
被験物質+PRP+アラキドン酸を加えたときの最大凝集率をBとする。
凝集阻害率(%)をCとすると
C=100−B/A×100
前記試験方法において、被験物質100μgを添加した条件下で血小板凝集阻害活性を測定した。さらに活性が比較的高いものについて、被験物質50μg、10μgを添加した条件下での血小板凝集阻害活性を測定した。
錠剤配合例(質量比)
──────────────────────
本発明のアラキドン酸代謝抑制剤 5.0
6%HPC乳糖 80.0
ステアリン酸マグネシウム 4.0
バレイショデンプン 6.0
──────────────────────
軟膏剤配合例(質量比)
─────────────────────────
白色ワセリン 20.0
ステアリルアルコール 22.0
プロピレングリコール 12.0
ラウリル硫酸ナトリウム 1.5
パラベン 0.2
本発明のアラキドン酸代謝抑制剤 5.0
精製水 39.3
─────────────────────────
入浴剤配合例(質量比)
――――――――――――――――――――――─
炭酸水素ナトリウム 50.0
硫酸ナトリウム 46.0
本発明のアラキドン酸代謝抑制剤 0.3
香料 0.7
色素 3.0
───────────────────────
アイスクリーム配合例(質量比)
────────────────────────
全脂練乳 10.0
生クリーム 9.4
無塩バター 2.0
脱脂粉乳 3.4
砂糖 12.0
安定剤 0.3
乳化剤 0.2
pH調整剤 0.1
カラメル色素 0.1
本発明のアラキドン酸代謝抑制剤 0.01
香料 0.01
水 49.0
────────────────────────
クッキー生地配合例(質量比)
────────────────────────
薄力粉 62.5
全粒粉 37.5
ショートニング 30.0
全卵 30.0
砂糖 20.0
水飴 1.0
脱脂粉乳 5.0
食塩 1.2
食用油脂 30.0
重炭酸ソーダ 1.0
重炭酸アンモニウム 1.0
本発明のアラキドン酸代謝抑制剤 0.01
香料 0.3
水 11.0
────────────────────────
チョコレート配合例(質量比)
─────────────────────────
カカオ液 12.0
カカオバター 24.0
ショ糖 33.0
フルクリームミルクパウダー 19.0
スキムミルクパウダー 11.4
レシチン 0.5
本発明のアラキドン酸代謝抑制剤 0.01
香料 0.1
─────────────────────────
ノンオイルドレッシング配合例(質量比)
─────────────────────────
濃口醤油 10.0
醸造酢 6.0
リンゴ酢 5.0
レモン果汁 4.0
液糖 7.0
食塩 2.0
調味料 7.0
本発明のアラキドン酸代謝抑制剤 0.01
香料 0.2
水 50.0
─────────────────────────
飲料配合例(質量比)
――――――――――――――――――――――───
果糖ぶどう糖液糖 60.0
アップル透明果汁 4.3
クエン酸 2.3
クエン酸三ナトリウム 0.8
アスコルビン酸 0.2
スクラロース 0.03
アセスルファムカリウム 0.02
香料 0.99
本発明のアラキドン酸代謝抑制剤 0.01
水 31.0
――――――――――――――――――――――───
チューインガム配合例(質量比)
――――――――――――――――――――――─
ガムベース 20.0
砂糖 60.0
ブドウ糖 10.0
水飴 8.0
グリセリン 5.0
香料 0.7
本発明のアラキドン酸代謝抑制剤 0.3
───────────────────────
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