NO300733B1 - Fremgangsmåte for fremstilling av rene isoflavonderivater - Google Patents
Fremgangsmåte for fremstilling av rene isoflavonderivater Download PDFInfo
- Publication number
- NO300733B1 NO300733B1 NO914786A NO914786A NO300733B1 NO 300733 B1 NO300733 B1 NO 300733B1 NO 914786 A NO914786 A NO 914786A NO 914786 A NO914786 A NO 914786A NO 300733 B1 NO300733 B1 NO 300733B1
- Authority
- NO
- Norway
- Prior art keywords
- general formula
- product
- vii
- indicated above
- reaction mixture
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 23
- 150000002515 isoflavone derivatives Chemical class 0.000 title claims abstract description 6
- 229930012930 isoflavone derivative Natural products 0.000 title claims abstract description 5
- 238000002360 preparation method Methods 0.000 title claims abstract 3
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 230000002152 alkylating effect Effects 0.000 claims abstract description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 43
- 239000000047 product Substances 0.000 claims description 33
- 239000011541 reaction mixture Substances 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 17
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 10
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 6
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 claims description 5
- 239000006227 byproduct Substances 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- -1 isopropyl halide Chemical class 0.000 claims description 5
- 239000012454 non-polar solvent Substances 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000002798 polar solvent Substances 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000007363 ring formation reaction Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000000717 retained effect Effects 0.000 claims 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 abstract 1
- WMKOZARWBMFKAS-UHFFFAOYSA-N 7-hydroxyisoflavone Chemical class C=1C(O)=CC=C(C2=O)C=1OC=C2C1=CC=CC=C1 WMKOZARWBMFKAS-UHFFFAOYSA-N 0.000 description 26
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 16
- MEIOIMGKPPMDKW-UHFFFAOYSA-N 7-ethoxy-3-phenylchromen-4-one Chemical class C=1C(OCC)=CC=C(C2=O)C=1OC=C2C1=CC=CC=C1 MEIOIMGKPPMDKW-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000004128 high performance liquid chromatography Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- VFQKAJVKZKHVPD-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-phenylethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=CC=C1 VFQKAJVKZKHVPD-UHFFFAOYSA-N 0.000 description 6
- SFBODOKJTYAUCM-UHFFFAOYSA-N Ipriflavone Chemical compound C=1C(OC(C)C)=CC=C(C2=O)C=1OC=C2C1=CC=CC=C1 SFBODOKJTYAUCM-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 235000011181 potassium carbonates Nutrition 0.000 description 6
- 238000011109 contamination Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000004611 spectroscopical analysis Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 229960005431 ipriflavone Drugs 0.000 description 4
- 150000003335 secondary amines Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 2
- VFZIJLPRJAQGFO-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-7-hydroxychromen-4-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=COC2=CC(O)=CC=C2C1=O VFZIJLPRJAQGFO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 239000011736 potassium bicarbonate Substances 0.000 description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- HGLLHSYBXHPWND-UHFFFAOYSA-N 1,3-bis(2,4-dihydroxyphenyl)-1,3-bis(3,4-dimethoxyphenyl)propan-2-one Chemical compound OC1=C(C=CC(=C1)O)C(C1=CC(=C(C=C1)OC)OC)C(=O)C(C1=CC(=C(C=C1)OC)OC)C1=C(C=C(C=C1)O)O HGLLHSYBXHPWND-UHFFFAOYSA-N 0.000 description 1
- IBMIVKGDPUAYAV-UHFFFAOYSA-N 1,3-bis(2-hydroxyphenyl)-1,3-diphenylpropan-2-one Chemical compound OC1=CC=CC=C1C(C=1C=CC=CC=1)C(=O)C(C=1C(=CC=CC=1)O)C1=CC=CC=C1 IBMIVKGDPUAYAV-UHFFFAOYSA-N 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- CJWQYWQDLBZGPD-UHFFFAOYSA-N isoflavone Natural products C1=C(OC)C(OC)=CC(OC)=C1C1=COC2=C(C=CC(C)(C)O3)C3=C(OC)C=C2C1=O CJWQYWQDLBZGPD-UHFFFAOYSA-N 0.000 description 1
- 235000008696 isoflavones Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- ZNSWGHZWUUFFKV-UHFFFAOYSA-N piperidine;pyridine Chemical compound C1CCNCC1.C1=CC=NC=C1 ZNSWGHZWUUFFKV-UHFFFAOYSA-N 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/34—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 3 only
- C07D311/36—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 3 only not hydrogenated in the hetero ring, e.g. isoflavones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
-
- 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
- A61P3/02—Nutrients, e.g. vitamins, minerals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Diabetes (AREA)
- Nutrition Science (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Saccharide Compounds (AREA)
- Diaphragms For Electromechanical Transducers (AREA)
- Train Traffic Observation, Control, And Security (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/HU1990/000023 WO1991015483A1 (fr) | 1990-04-06 | 1990-04-06 | Procede ameliore de preparation de derives substitues d'isoflavone |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO914786D0 NO914786D0 (no) | 1991-12-05 |
| NO914786L NO914786L (no) | 1991-12-05 |
| NO300733B1 true NO300733B1 (no) | 1997-07-14 |
Family
ID=10980899
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO914786A NO300733B1 (no) | 1990-04-06 | 1991-12-05 | Fremgangsmåte for fremstilling av rene isoflavonderivater |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US5247102A (fr) |
| EP (1) | EP0478558B1 (fr) |
| JP (1) | JPH089610B2 (fr) |
| KR (1) | KR0149172B1 (fr) |
| AT (1) | ATE101143T1 (fr) |
| AU (1) | AU631860B2 (fr) |
| CA (1) | CA2058619C (fr) |
| DE (1) | DE69006502T2 (fr) |
| DK (1) | DK0478558T3 (fr) |
| FI (1) | FI915741A0 (fr) |
| HK (1) | HK1003995A1 (fr) |
| LT (1) | LT3463B (fr) |
| NO (1) | NO300733B1 (fr) |
| RU (1) | RU2036918C1 (fr) |
| WO (1) | WO1991015483A1 (fr) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5002603A (en) * | 1989-12-04 | 1991-03-26 | Board Of Trustees Operating Michigan State University | Method and compositions for stimulating vesicular-arbuscular mycorrhizal fungi |
| US5204369A (en) * | 1991-07-01 | 1993-04-20 | The Endowment For Research In Human Biology | Method for the inhibition of aldh-i useful in the treatment of alcohol dependence or alcohol abuse |
| FR2689127B1 (fr) * | 1992-03-31 | 1994-05-06 | Adir Cie | Nouvelles 3', 5' -ditertbutyl-4'-hydroxy flavones, leur procede de preparation et les compositions pharmaceutiques les renfermant. |
| ATE275959T1 (de) | 1992-05-19 | 2004-10-15 | Graham Edmund Kelly | Verwendung von isoflavon phyto-östrogen extrakten von soja oder klee |
| HUT68558A (en) * | 1993-07-20 | 1995-06-28 | Chinoin Gyogyszer Es Vegyeszet | Method for preparing isoflavon derivatives |
| US5670632A (en) * | 1996-01-18 | 1997-09-23 | Acds Technologies, Ltd. | Process for obtaining an isoflavone concentrate from a soybean extract |
| AUPO203996A0 (en) * | 1996-08-30 | 1996-09-26 | Novogen Research Pty Ltd | Therapeutic uses |
| US6146668A (en) | 1997-04-28 | 2000-11-14 | Novogen, Inc. | Preparation of isoflavones from legumes |
| US6255497B1 (en) | 1997-04-29 | 2001-07-03 | The Endowment For Research In Human Biology, Inc. | Method for the inhibition of ALDH-I useful in the treatment of alcohol dependence or alcohol abuse |
| WO1998050026A1 (fr) * | 1997-05-01 | 1998-11-12 | Novogen Inc | Traitement ou prevention des symptomes menopausiques et de l'osteoporose |
| AUPP112497A0 (en) * | 1997-12-24 | 1998-01-22 | Novogen Research Pty Ltd | Compositions and method for protecting skin from UV induced immunosupression and skin damage |
| IT1298619B1 (it) * | 1998-03-10 | 2000-01-12 | Erregierre Spa | Processo di preparazione dell'epriflavone |
| AUPP260798A0 (en) * | 1998-03-26 | 1998-04-23 | Novogen Research Pty Ltd | Treatment of medical related conditions with isoflavone containing extracts of clover |
| AUPQ266199A0 (en) * | 1999-09-06 | 1999-09-30 | Novogen Research Pty Ltd | Compositions and therapeutic methods involving isoflavones and analogues thereof |
| US20090233999A1 (en) * | 1999-09-06 | 2009-09-17 | Novogen Research Pty Ltd | Compositions and therapeutic methods involving isoflavones and analogues thereof |
| AUPQ520300A0 (en) * | 2000-01-21 | 2000-02-17 | Novogen Research Pty Ltd | Food product and process |
| AUPR363301A0 (en) * | 2001-03-08 | 2001-04-05 | Novogen Research Pty Ltd | Dimeric isoflavones |
| US20050119301A1 (en) * | 2001-03-16 | 2005-06-02 | Alan Husband | Treatment of restenosis |
| US6818668B2 (en) | 2002-04-12 | 2004-11-16 | Biotest Laboratories, Llc | 5-alkyl-7-alkylcarbonate-isoflavone ester and related method |
| US7368434B2 (en) | 2002-06-27 | 2008-05-06 | The Endowment For Research In Human Biology, Inc. | Compounds useful for the inhibition of ALDH |
| US7468445B2 (en) | 2002-08-07 | 2008-12-23 | University Of Mississippi | Antigiardial agents and use thereof |
| US8158810B2 (en) | 2006-07-27 | 2012-04-17 | Gilead Sciences, Inc. | ALDH-2 inhibitors in the treatment of addiction |
| TWI324514B (en) * | 2008-02-26 | 2010-05-11 | Univ Kaohsiung Medical | Isoflavone derivatives and pharmaceutical compositions comprising the same |
| TWI365071B (en) * | 2008-02-26 | 2012-06-01 | Univ Kaohsiung Medical | Isoxazole derivatives and pharmaceutical compositions comprising the same |
| CN103145673B (zh) * | 2011-12-06 | 2015-05-20 | 安徽贝克生物制药有限公司 | 黄豆苷元衍生物及其药学上可接受的盐 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA201219A (fr) | 1920-06-22 | Hippolyte Louis Sizaire Maurice | Ressort lamine a graisseur | |
| CA193010A (fr) | 1919-04-02 | 1919-09-30 | Alvin A. Ritcheson | Carrosserie d'automobile |
| HU162377B (fr) * | 1970-05-27 | 1973-02-28 | ||
| GB1495305A (en) * | 1975-09-12 | 1977-12-14 | Pfizer Ltd | 3-phenyl-4-oxo-4h-benzopyran derivatives |
| GB1495189A (en) * | 1975-09-12 | 1977-12-14 | Pfizer Ltd | 4-oxo-4h-benzopyran derivatives and process for their preparation |
| US4644012A (en) * | 1983-12-21 | 1987-02-17 | Takeda Chemical Industries, Ltd. | Treatment for osteoporosis |
| JPS60132976A (ja) * | 1983-12-21 | 1985-07-16 | Takeda Chem Ind Ltd | 新規３−フエニル−４ｈ−１−ベンゾピラン−４−オン誘導体 |
| US5002603A (en) * | 1989-12-04 | 1991-03-26 | Board Of Trustees Operating Michigan State University | Method and compositions for stimulating vesicular-arbuscular mycorrhizal fungi |
-
1990
- 1990-04-06 JP JP2506037A patent/JPH089610B2/ja not_active Expired - Lifetime
- 1990-04-06 US US07/778,927 patent/US5247102A/en not_active Expired - Fee Related
- 1990-04-06 KR KR1019910701792A patent/KR0149172B1/ko not_active IP Right Cessation
- 1990-04-06 CA CA002058619A patent/CA2058619C/fr not_active Expired - Fee Related
- 1990-04-06 EP EP90906260A patent/EP0478558B1/fr not_active Expired - Lifetime
- 1990-04-06 AT AT90906260T patent/ATE101143T1/de not_active IP Right Cessation
- 1990-04-06 WO PCT/HU1990/000023 patent/WO1991015483A1/fr active IP Right Grant
- 1990-04-06 AU AU54274/90A patent/AU631860B2/en not_active Ceased
- 1990-04-06 DK DK90906260.6T patent/DK0478558T3/da active
- 1990-04-06 DE DE69006502T patent/DE69006502T2/de not_active Expired - Fee Related
-
1991
- 1991-12-05 RU SU915010742A patent/RU2036918C1/ru active
- 1991-12-05 FI FI915741A patent/FI915741A0/fi unknown
- 1991-12-05 NO NO914786A patent/NO300733B1/no unknown
-
1993
- 1993-07-13 LT LTIP779A patent/LT3463B/lt unknown
-
1998
- 1998-04-16 HK HK98103150A patent/HK1003995A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FI915741A0 (fi) | 1991-12-05 |
| WO1991015483A1 (fr) | 1991-10-17 |
| DK0478558T3 (da) | 1994-05-02 |
| ATE101143T1 (de) | 1994-02-15 |
| KR0149172B1 (ko) | 1998-10-15 |
| US5247102A (en) | 1993-09-21 |
| LT3463B (en) | 1995-10-25 |
| CA2058619C (fr) | 1999-05-04 |
| NO914786D0 (no) | 1991-12-05 |
| EP0478558A1 (fr) | 1992-04-08 |
| DE69006502D1 (de) | 1994-03-17 |
| EP0478558B1 (fr) | 1994-02-02 |
| HK1003995A1 (en) | 1998-11-13 |
| NO914786L (no) | 1991-12-05 |
| JPH04507085A (ja) | 1992-12-10 |
| RU2036918C1 (ru) | 1995-06-09 |
| KR920701192A (ko) | 1992-08-11 |
| JPH089610B2 (ja) | 1996-01-31 |
| AU631860B2 (en) | 1992-12-10 |
| AU5427490A (en) | 1991-10-30 |
| DE69006502T2 (de) | 1994-05-19 |
| CA2058619A1 (fr) | 1991-10-07 |
| LTIP779A (en) | 1995-01-31 |
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