JP2008239513A5 - - Google Patents
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- JP2008239513A5 JP2008239513A5 JP2007079311A JP2007079311A JP2008239513A5 JP 2008239513 A5 JP2008239513 A5 JP 2008239513A5 JP 2007079311 A JP2007079311 A JP 2007079311A JP 2007079311 A JP2007079311 A JP 2007079311A JP 2008239513 A5 JP2008239513 A5 JP 2008239513A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- hydroxyl group
- formula
- halogen atom
- protected
- 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
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 62
- 150000001875 compounds Chemical class 0.000 claims description 40
- 125000005843 halogen group Chemical group 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000002252 acyl group Chemical group 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 17
- 239000000010 aprotic solvent Substances 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 125000004185 ester group Chemical group 0.000 claims description 13
- -1 azodicarboxylic amide Chemical class 0.000 claims description 10
- 229930185379 chafuroside Natural products 0.000 claims description 9
- 125000001033 ether group Chemical group 0.000 claims description 8
- 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 claims description 7
- 239000008103 glucose Substances 0.000 claims description 7
- 229930003944 flavone Natural products 0.000 claims description 6
- 235000011949 flavones Nutrition 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000003586 protic polar solvent Substances 0.000 claims description 5
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical group C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 4
- 150000002213 flavones Chemical class 0.000 claims description 4
- VBQCHPIMZGQLAZ-UHFFFAOYSA-N phosphorane Chemical class [PH5] VBQCHPIMZGQLAZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 31
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- 125000006239 protecting group Chemical class 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 229940126214 compound 3 Drugs 0.000 description 3
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- USVVENVKYJZFMW-ONEGZZNKSA-N (e)-carboxyiminocarbamic acid Chemical compound OC(=O)\N=N\C(O)=O USVVENVKYJZFMW-ONEGZZNKSA-N 0.000 description 2
- 206010012438 Dermatitis atopic Diseases 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 238000006751 Mitsunobu reaction Methods 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 235000006468 Thea sinensis Nutrition 0.000 description 2
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 239000002260 anti-inflammatory agent Substances 0.000 description 2
- 229940124599 anti-inflammatory drug Drugs 0.000 description 2
- 201000008937 atopic dermatitis Diseases 0.000 description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 229940125773 compound 10 Drugs 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- 238000010511 deprotection reaction Methods 0.000 description 2
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 2
- 150000002212 flavone derivatives Chemical class 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- 229930182470 glycoside Natural products 0.000 description 2
- 150000002338 glycosides Chemical class 0.000 description 2
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 235000020333 oolong tea Nutrition 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- 150000003431 steroids Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- VLSDXINSOMDCBK-BQYQJAHWSA-N (E)-1,1'-azobis(N,N-dimethylformamide) Chemical compound CN(C)C(=O)\N=N\C(=O)N(C)C VLSDXINSOMDCBK-BQYQJAHWSA-N 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- AQSCHALQLXXKKC-UHFFFAOYSA-N 4-phenylmethoxybenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OCC1=CC=CC=C1 AQSCHALQLXXKKC-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
- MYXNWGACZJSMBT-RAFLFOFHSA-N C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C=C(C(=C3O)[C@H]4[C@H](C([C@@H](C(O4)CO)O)O)O)O)O Chemical compound C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C=C(C(=C3O)[C@H]4[C@H](C([C@@H](C(O4)CO)O)O)O)O)O MYXNWGACZJSMBT-RAFLFOFHSA-N 0.000 description 1
- FNFULEVKLPATBU-VJXOUQPKSA-N C1=CC=C(C=C1)COCC2[C@H](C([C@@H]([C@@H](O2)C3=C(C=C(C(=C3OCC4=CC=CC=C4)C(=O)CC(=O)C5=CC=C(C=C5)OCC6=CC=CC=C6)O)OCC7=CC=CC=C7)OCC8=CC=CC=C8)OCC9=CC=CC=C9)OCC1=CC=CC=C1 Chemical compound C1=CC=C(C=C1)COCC2[C@H](C([C@@H]([C@@H](O2)C3=C(C=C(C(=C3OCC4=CC=CC=C4)C(=O)CC(=O)C5=CC=C(C=C5)OCC6=CC=CC=C6)O)OCC7=CC=CC=C7)OCC8=CC=CC=C8)OCC9=CC=CC=C9)OCC1=CC=CC=C1 FNFULEVKLPATBU-VJXOUQPKSA-N 0.000 description 1
- MJLULROVRJQOKB-CFAICBQOSA-N C1=CC=C(C=C1)COCC2[C@H](C([C@@H]([C@@H](O2)C3=C(C=C4C(=C3O)C(=O)C=C(O4)C5=CC=C(C=C5)OCC6=CC=CC=C6)OCC7=CC=CC=C7)OCC8=CC=CC=C8)OCC9=CC=CC=C9)OCC1=CC=CC=C1 Chemical compound C1=CC=C(C=C1)COCC2[C@H](C([C@@H]([C@@H](O2)C3=C(C=C4C(=C3O)C(=O)C=C(O4)C5=CC=C(C=C5)OCC6=CC=CC=C6)OCC7=CC=CC=C7)OCC8=CC=CC=C8)OCC9=CC=CC=C9)OCC1=CC=CC=C1 MJLULROVRJQOKB-CFAICBQOSA-N 0.000 description 1
- ODEKREWSSQOOJI-UXQCHDOSSA-N CC(=O)C1=C(C=C(C(=C1O)[C@H]2[C@H](C([C@@H](C(O2)COCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5)OCC6=CC=CC=C6)OCC7=CC=CC=C7)O[Si](C8=CC=CC=C8)(C9=CC=CC=C9)C(C)(C)C Chemical compound CC(=O)C1=C(C=C(C(=C1O)[C@H]2[C@H](C([C@@H](C(O2)COCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5)OCC6=CC=CC=C6)OCC7=CC=CC=C7)O[Si](C8=CC=CC=C8)(C9=CC=CC=C9)C(C)(C)C ODEKREWSSQOOJI-UXQCHDOSSA-N 0.000 description 1
- KHKKLEJJZHGNCT-PSRMNSPFSA-N CC(=O)C1=C(C=C(C(=C1OCC2=CC=CC=C2)[C@H]3[C@H](C([C@@H](C(O3)COCC4=CC=CC=C4)OCC5=CC=CC=C5)OCC6=CC=CC=C6)OCC7=CC=CC=C7)OCC8=CC=CC=C8)O[Si](C9=CC=CC=C9)(C1=CC=CC=C1)C(C)(C)C Chemical compound CC(=O)C1=C(C=C(C(=C1OCC2=CC=CC=C2)[C@H]3[C@H](C([C@@H](C(O3)COCC4=CC=CC=C4)OCC5=CC=CC=C5)OCC6=CC=CC=C6)OCC7=CC=CC=C7)OCC8=CC=CC=C8)O[Si](C9=CC=CC=C9)(C1=CC=CC=C1)C(C)(C)C KHKKLEJJZHGNCT-PSRMNSPFSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- GNSGBBSUSWZXKD-UHFFFAOYSA-N benzotriazol-1-yl-(4-phenylmethoxyphenyl)methanone Chemical compound N1=NC2=CC=CC=C2N1C(=O)C(C=C1)=CC=C1OCC1=CC=CC=C1 GNSGBBSUSWZXKD-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- DLIJPAHLBJIQHE-UHFFFAOYSA-N butylphosphane Chemical compound CCCCP DLIJPAHLBJIQHE-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 description 1
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2007079311A JP2008239513A (ja) | 2007-03-26 | 2007-03-26 | 効率的フラボン構築に基づくＣｈａｆｕｒｏｓｉｄｅの新規製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2007079311A JP2008239513A (ja) | 2007-03-26 | 2007-03-26 | 効率的フラボン構築に基づくＣｈａｆｕｒｏｓｉｄｅの新規製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008239513A JP2008239513A (ja) | 2008-10-09 |
| JP2008239513A5 true JP2008239513A5 (https=) | 2010-04-08 |
Family
ID=39911274
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007079311A Pending JP2008239513A (ja) | 2007-03-26 | 2007-03-26 | 効率的フラボン構築に基づくＣｈａｆｕｒｏｓｉｄｅの新規製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2008239513A (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102272129B (zh) * | 2009-01-03 | 2014-10-08 | 静冈县公立大学法人 | 硫酸化c-糖苷及其分离方法以及合成方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10104350A1 (de) * | 2001-02-01 | 2002-08-14 | Merck Patent Gmbh | Verfahren zur Herstellung von Flavon Derivaten |
| JP2006176407A (ja) * | 2003-04-18 | 2006-07-06 | Daiichi Asubio Pharma Co Ltd | 新規フラボン誘導体、その製造法およびそれらを含む医薬組成物 |
| JP2005289888A (ja) * | 2004-03-31 | 2005-10-20 | Suntory Ltd | フラボンｃ配糖体誘導体の製造方法 |
| JP2005314260A (ja) * | 2004-04-28 | 2005-11-10 | Japan Science & Technology Agency | フラボンｃ配糖体の製法 |
| JP2006008626A (ja) * | 2004-06-28 | 2006-01-12 | Daiichi Asubio Pharma Co Ltd | フラボン誘導体の製造法ならびにフラボン誘導体およびそれを含む医薬組成物 |
-
2007
- 2007-03-26 JP JP2007079311A patent/JP2008239513A/ja active Pending
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