JP4309769B2 - 新規なグルコピラノサイド、その分離方法、それを含む薬物及びその使用方法 - Google Patents
新規なグルコピラノサイド、その分離方法、それを含む薬物及びその使用方法 Download PDFInfo
- Publication number
- JP4309769B2 JP4309769B2 JP2003584049A JP2003584049A JP4309769B2 JP 4309769 B2 JP4309769 B2 JP 4309769B2 JP 2003584049 A JP2003584049 A JP 2003584049A JP 2003584049 A JP2003584049 A JP 2003584049A JP 4309769 B2 JP4309769 B2 JP 4309769B2
- Authority
- JP
- Japan
- Prior art keywords
- glucopyranoside
- solvent
- hydroxy
- rukopiranosaido
- hydroxybenzylbenzofuran
- 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.)
- Expired - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 23
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 title claims abstract description 9
- 239000003814 drug Substances 0.000 title claims description 16
- 229940079593 drug Drugs 0.000 title claims description 14
- 238000000926 separation method Methods 0.000 title claims description 4
- MCHGHPIHLAZAFH-UHFFFAOYSA-N pteroside Natural products OC1C(O)C(O)C(CO)OC1C1=C(O)C=CC2=C1OC(CC=1C=CC(O)=CC=1)=C2 MCHGHPIHLAZAFH-UHFFFAOYSA-N 0.000 claims abstract description 25
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 67
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 42
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 39
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 25
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 22
- 239000000284 extract Substances 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 17
- 239000003960 organic solvent Substances 0.000 claims description 14
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 11
- 238000003820 Medium-pressure liquid chromatography Methods 0.000 claims description 10
- 238000003818 flash chromatography Methods 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 241000196324 Embryophyta Species 0.000 claims description 6
- 238000004587 chromatography analysis Methods 0.000 claims description 6
- 230000037396 body weight Effects 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 4
- 239000002798 polar solvent Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 238000010298 pulverizing process Methods 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims 2
- 241000533793 Tipuana tipu Species 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 15
- 240000008976 Pterocarpus marsupium Species 0.000 abstract 1
- 235000010453 Pterocarpus marsupium Nutrition 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 244000086363 Pterocarpus indicus Species 0.000 description 19
- 235000009984 Pterocarpus indicus Nutrition 0.000 description 17
- 230000003178 anti-diabetic effect Effects 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 6
- 239000006286 aqueous extract Substances 0.000 description 5
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 4
- 239000012259 ether extract Substances 0.000 description 4
- 239000002024 ethyl acetate extract Substances 0.000 description 4
- OBWHQJYOOCRPST-UHFFFAOYSA-N 3,4',7-trihydroxyflavone Chemical compound C1=CC(O)=CC=C1C1=C(O)C(=O)C2=CC=C(O)C=C2O1 OBWHQJYOOCRPST-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 150000001720 carbohydrates Chemical group 0.000 description 3
- -1 etc. Substances 0.000 description 3
- IQTGAKWQIFFPQX-UHFFFAOYSA-N marsupsin Chemical compound O=C1C=2C(OC)=CC(O)=CC=2OC1(O)CC1=CC=C(O)C=C1 IQTGAKWQIFFPQX-UHFFFAOYSA-N 0.000 description 3
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-3',4',5,7-Tetrahydroxy-2,3-trans-flavan-3-ol Natural products C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 description 2
- PFTAWBLQPZVEMU-UKRRQHHQSA-N (-)-epicatechin Chemical group C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-UKRRQHHQSA-N 0.000 description 2
- 229930013783 (-)-epicatechin Natural products 0.000 description 2
- 235000007355 (-)-epicatechin Nutrition 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical class C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical class CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229940127003 anti-diabetic drug Drugs 0.000 description 2
- 239000003472 antidiabetic agent Substances 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- JBQATDIMBVLPRB-UHFFFAOYSA-N isoliquiritigenin Natural products OC1=CC(O)=CC=C1C1OC2=CC(O)=CC=C2C(=O)C1 JBQATDIMBVLPRB-UHFFFAOYSA-N 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- JCPGMXJLFWGRMZ-UHFFFAOYSA-N 1-(2-hydroxyphenyl)-3-phenylpropan-1-one Chemical compound OC1=CC=CC=C1C(=O)CCC1=CC=CC=C1 JCPGMXJLFWGRMZ-UHFFFAOYSA-N 0.000 description 1
- WNYHMEYKAGKERM-UHFFFAOYSA-N 2-[(4-hydroxyphenyl)methyl]-1-benzofuran-6-ol Chemical compound OC1=CC=C(CC=2OC3=C(C=2)C=CC(=C3)O)C=C1 WNYHMEYKAGKERM-UHFFFAOYSA-N 0.000 description 1
- FBUPXHQDNXCVLC-UHFFFAOYSA-N 4',5-Di-Me ether,7-O-alpha-L-rhamnopyranoside-4',5,7-Trihydroxy-8-methylisoflavone Natural products COc1ccc(cc1)C2=COc3c(C)c(OC4OC(C)C(O)C(O)C4O)cc(OC)c3C2=O FBUPXHQDNXCVLC-UHFFFAOYSA-N 0.000 description 1
- LCAWNFIFMLXZPQ-UHFFFAOYSA-N 4',7-dihydroxyflavone Chemical compound C1=CC(O)=CC=C1C1=CC(=O)C2=CC=C(O)C=C2O1 LCAWNFIFMLXZPQ-UHFFFAOYSA-N 0.000 description 1
- HBFNWMJHTGIQRB-UHFFFAOYSA-N 4-[2-hydroxy-3-(4-hydroxyphenyl)propyl]benzene-1,3-diol Chemical compound C=1C=C(O)C=C(O)C=1CC(O)CC1=CC=C(O)C=C1 HBFNWMJHTGIQRB-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 1
- TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 description 1
- PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 description 1
- 210000002237 B-cell of pancreatic islet Anatomy 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- IQTGAKWQIFFPQX-INIZCTEOSA-N Carpusin Natural products O(C)c1c2C(=O)[C@](O)(Cc3ccc(O)cc3)Oc2cc(O)c1 IQTGAKWQIFFPQX-INIZCTEOSA-N 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- RKWGIWYCVPQPMF-UHFFFAOYSA-N Chloropropamide Chemical compound CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 RKWGIWYCVPQPMF-UHFFFAOYSA-N 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 241000220485 Fabaceae Species 0.000 description 1
- FURUXTVZLHCCNA-UHFFFAOYSA-N Liquiritigenin Natural products C1=CC(O)=CC=C1C1OC2=CC(O)=CC=C2C(=O)C1 FURUXTVZLHCCNA-UHFFFAOYSA-N 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 240000000513 Santalum album Species 0.000 description 1
- 235000008632 Santalum album Nutrition 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229960001761 chlorpropamide Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- PXLWOFBAEVGBOA-UHFFFAOYSA-N dihydrochalcone Natural products OC1C(O)C(O)C(CO)OC1C1=C(O)C=CC(C(=O)CC(O)C=2C=CC(O)=CC=2)=C1O PXLWOFBAEVGBOA-UHFFFAOYSA-N 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000012156 elution solvent Substances 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- NBEMQPLNBYYUAZ-UHFFFAOYSA-N ethyl acetate;propan-2-one Chemical compound CC(C)=O.CCOC(C)=O NBEMQPLNBYYUAZ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- LYINKTVZUSKQEQ-UHFFFAOYSA-N furan-3-one Chemical compound O=C1COC=C1 LYINKTVZUSKQEQ-UHFFFAOYSA-N 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000001052 heteronuclear multiple bond coherence spectrum Methods 0.000 description 1
- PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229930013032 isoflavonoid Natural products 0.000 description 1
- 150000003817 isoflavonoid derivatives Chemical class 0.000 description 1
- 235000012891 isoflavonoids Nutrition 0.000 description 1
- DXDRHHKMWQZJHT-FPYGCLRLSA-N isoliquiritigenin Chemical compound C1=CC(O)=CC=C1\C=C\C(=O)C1=CC=C(O)C=C1O DXDRHHKMWQZJHT-FPYGCLRLSA-N 0.000 description 1
- 235000008718 isoliquiritigenin Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- FURUXTVZLHCCNA-AWEZNQCLSA-N liquiritigenin Chemical compound C1=CC(O)=CC=C1[C@H]1OC2=CC(O)=CC=C2C(=O)C1 FURUXTVZLHCCNA-AWEZNQCLSA-N 0.000 description 1
- NTQHBBDWBRQLIA-UHFFFAOYSA-N marsupol Natural products C=1C=C(O)C=CC=1C(O)(C)C(O)C1=CC=C(O)C=C1 NTQHBBDWBRQLIA-UHFFFAOYSA-N 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 206010040872 skin infection Diseases 0.000 description 1
- GSZUGBAEBARHAW-UHFFFAOYSA-N sophoraflavone B Natural products OC1C(O)C(O)C(CO)OC1OC1=CC=C(C=2OC3=CC(O)=CC=C3C(=O)C=2)C=C1 GSZUGBAEBARHAW-UHFFFAOYSA-N 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 208000004371 toothache Diseases 0.000 description 1
- 208000019206 urinary tract infection Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
- C07H7/06—Heterocyclic radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biochemistry (AREA)
- Obesity (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Genetics & Genomics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Saccharide Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/IN2002/000105 WO2003087093A1 (en) | 2002-04-08 | 2002-04-08 | Novel glucopyranoside, process for isolation thereof, pharmaceutical composition containing same and use thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005528398A JP2005528398A (ja) | 2005-09-22 |
| JP2005528398A5 JP2005528398A5 (enExample) | 2009-05-07 |
| JP4309769B2 true JP4309769B2 (ja) | 2009-08-05 |
Family
ID=29227416
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003584049A Expired - Fee Related JP4309769B2 (ja) | 2002-04-08 | 2002-04-08 | 新規なグルコピラノサイド、その分離方法、それを含む薬物及びその使用方法 |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP1495019B1 (enExample) |
| JP (1) | JP4309769B2 (enExample) |
| CN (1) | CN1280290C (enExample) |
| AT (1) | ATE399778T1 (enExample) |
| AU (1) | AU2002246317A1 (enExample) |
| DE (1) | DE60227421D1 (enExample) |
| WO (1) | WO2003087093A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2567571T3 (es) * | 2003-03-14 | 2016-04-25 | Astellas Pharma Inc. | Derivados de C-glucósido y sales de los mismos |
| TW200524951A (en) | 2003-08-01 | 2005-08-01 | Janssen Pharmaceutica Nv | Substituted benzimidazole-, benztriazole-, and benzimidazolone-O-glucosides |
| CA2549015A1 (en) | 2003-08-01 | 2005-02-10 | Janssen Pharmaceutica N.V. | Substituted fused heterocyclic c-glycosides |
| AU2004261264A1 (en) | 2003-08-01 | 2005-02-10 | Janssen Pharmaceutica N.V. | Substituted indazole-O-glucosides |
| TW200526678A (en) | 2003-08-01 | 2005-08-16 | Janssen Pharmaceutica Nv | Substituted indole-O-glucosides |
| EP1721904A4 (en) * | 2004-03-04 | 2010-07-14 | Kissei Pharmaceutical | HETEROCYCLIC DERIVED FADE; MEDICAL COMPOSITION CONTAINING THE DERIVATIVE AND MEDICAL USE |
| RU2387663C2 (ru) * | 2004-03-04 | 2010-04-27 | Киссеи Фармасьютикал Ко., Лтд. | Конденсированные гетероциклические производные, содержащие их медицинские композиции и их медицинское применение |
| EP2105442A4 (en) | 2006-12-21 | 2013-01-23 | Astellas Pharma Inc | PROCESS FOR PREPARING A C-GLYCOSIDE DERIVATIVE AND SYNTHETIC INTERMEDIATE PRODUCT THEREFOR |
| TW201623321A (zh) * | 2014-05-13 | 2016-07-01 | 韓美藥品股份有限公司 | 雙環衍生物及包含其之藥學組成物 |
| CN106674311B (zh) * | 2016-12-27 | 2019-02-05 | 西安交通大学 | 一种苯并呋喃苷类化合物及其制备方法和应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6627611B2 (en) * | 2000-02-02 | 2003-09-30 | Kotobuki Pharmaceutical Co Ltd | C-glycosides and preparation of thereof as antidiabetic agents |
-
2002
- 2002-04-08 DE DE60227421T patent/DE60227421D1/de not_active Expired - Lifetime
- 2002-04-08 JP JP2003584049A patent/JP4309769B2/ja not_active Expired - Fee Related
- 2002-04-08 EP EP02714415A patent/EP1495019B1/en not_active Expired - Lifetime
- 2002-04-08 AU AU2002246317A patent/AU2002246317A1/en not_active Abandoned
- 2002-04-08 CN CNB028291042A patent/CN1280290C/zh not_active Expired - Fee Related
- 2002-04-08 AT AT02714415T patent/ATE399778T1/de not_active IP Right Cessation
- 2002-04-08 WO PCT/IN2002/000105 patent/WO2003087093A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| ATE399778T1 (de) | 2008-07-15 |
| JP2005528398A (ja) | 2005-09-22 |
| AU2002246317A1 (en) | 2003-10-27 |
| CN1280290C (zh) | 2006-10-18 |
| EP1495019A1 (en) | 2005-01-12 |
| WO2003087093A1 (en) | 2003-10-23 |
| CN1633432A (zh) | 2005-06-29 |
| EP1495019B1 (en) | 2008-07-02 |
| DE60227421D1 (de) | 2008-08-14 |
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