NO328444B1 - Hyperforinderivat, anvendelse derav og farmasoytisk sammensetning inneholdende det - Google Patents
Hyperforinderivat, anvendelse derav og farmasoytisk sammensetning inneholdende det Download PDFInfo
- Publication number
- NO328444B1 NO328444B1 NO20006230A NO20006230A NO328444B1 NO 328444 B1 NO328444 B1 NO 328444B1 NO 20006230 A NO20006230 A NO 20006230A NO 20006230 A NO20006230 A NO 20006230A NO 328444 B1 NO328444 B1 NO 328444B1
- Authority
- NO
- Norway
- Prior art keywords
- hyperforin
- extract
- pharmaceutical composition
- composition containing
- compounds
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 3
- 150000002448 hyperforins Chemical class 0.000 title abstract description 5
- 230000001430 anti-depressive effect Effects 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 239000003814 drug Substances 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 15
- -1 cinnamoyl residue Chemical group 0.000 claims description 12
- 239000000935 antidepressant agent Substances 0.000 claims description 6
- 229940005513 antidepressants Drugs 0.000 claims description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 230000000144 pharmacologic effect Effects 0.000 abstract description 2
- 125000002252 acyl group Chemical group 0.000 abstract 1
- IWBJJCOKGLUQIZ-HQKKAZOISA-N hyperforin Chemical compound OC1=C(CC=C(C)C)C(=O)[C@@]2(CC=C(C)C)C[C@H](CC=C(C)C)[C@](CCC=C(C)C)(C)[C@]1(C(=O)C(C)C)C2=O IWBJJCOKGLUQIZ-HQKKAZOISA-N 0.000 description 16
- QOVWXXKVLJOKNW-UHFFFAOYSA-N hyperforin Natural products CC(C)C(=O)C12CC(CC=C(C)C)(CC(CC=C(C)C)C1CCC=C(C)C)C(=C(CC=C(C)C)C2=O)O QOVWXXKVLJOKNW-UHFFFAOYSA-N 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000284 extract Substances 0.000 description 11
- 238000012360 testing method Methods 0.000 description 10
- 235000017309 Hypericum perforatum Nutrition 0.000 description 9
- 241000700159 Rattus Species 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 244000141009 Hypericum perforatum Species 0.000 description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000000605 extraction Methods 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000007903 gelatin capsule Substances 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 208000019901 Anxiety disease Diseases 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000546188 Hypericum Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000012675 alcoholic extract Substances 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 230000036506 anxiety Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000013270 controlled release Methods 0.000 description 2
- 238000011981 development test Methods 0.000 description 2
- 229960004801 imipramine Drugs 0.000 description 2
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000004321 preservation Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- RTHCYVBBDHJXIQ-MRXNPFEDSA-N (R)-fluoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-MRXNPFEDSA-N 0.000 description 1
- SJSOFNCYXJUNBT-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC(OC)=C1OC SJSOFNCYXJUNBT-UHFFFAOYSA-N 0.000 description 1
- BUHYMJLFRZAFBF-UHFFFAOYSA-N 3,4,5-trimethoxybenzoyl chloride Chemical compound COC1=CC(C(Cl)=O)=CC(OC)=C1OC BUHYMJLFRZAFBF-UHFFFAOYSA-N 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- 235000020759 St. John’s wort extract Nutrition 0.000 description 1
- 229930003268 Vitamin C Natural products 0.000 description 1
- BQNGEEDNZRILLS-HZLVCURZSA-N [(1r,5r,6r,7s)-6-methyl-1,3,7-tris(3-methylbut-2-enyl)-6-(4-methylpent-3-enyl)-5-(2-methylpropanoyl)-4,9-dioxo-2-bicyclo[3.3.1]non-2-enyl] 3,4,5-trimethoxybenzoate Chemical compound COC1=C(OC)C(OC)=CC(C(=O)OC=2[C@]3(CC=C(C)C)C(=O)[C@]([C@]([C@@H](CC=C(C)C)C3)(C)CCC=C(C)C)(C(=O)C(C)C)C(=O)C=2CC=C(C)C)=C1 BQNGEEDNZRILLS-HZLVCURZSA-N 0.000 description 1
- JZPNZEVHKFXJKG-NVGSILRDSA-N [(1r,5s,6r,7s)-6-methyl-1,3,7-tris(3-methylbut-2-enyl)-6-(4-methylpent-3-enyl)-5-(2-methylpropanoyl)-4,9-dioxo-2-bicyclo[3.3.1]non-2-enyl] acetate Chemical compound O=C1C(CC=C(C)C)=C(OC(C)=O)[C@@]2(CC=C(C)C)C[C@H](CC=C(C)C)[C@](CCC=C(C)C)(C)[C@@]1(C(=O)C(C)C)C2=O JZPNZEVHKFXJKG-NVGSILRDSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 230000000949 anxiolytic effect Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000000262 chemical ionisation mass spectrometry Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000469 ethanolic extract Substances 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 229930003944 flavone Natural products 0.000 description 1
- 150000002213 flavones Chemical class 0.000 description 1
- 235000011949 flavones Nutrition 0.000 description 1
- 229960002464 fluoxetine Drugs 0.000 description 1
- 239000002035 hexane extract Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- BTXNYTINYBABQR-UHFFFAOYSA-N hypericin Chemical compound C12=C(O)C=C(O)C(C(C=3C(O)=CC(C)=C4C=33)=O)=C2C3=C2C3=C4C(C)=CC(O)=C3C(=O)C3=C(O)C=C(O)C1=C32 BTXNYTINYBABQR-UHFFFAOYSA-N 0.000 description 1
- 229940005608 hypericin Drugs 0.000 description 1
- PHOKTTKFQUYZPI-UHFFFAOYSA-N hypericin Natural products Cc1cc(O)c2c3C(=O)C(=Cc4c(O)c5c(O)cc(O)c6c7C(=O)C(=Cc8c(C)c1c2c(c78)c(c34)c56)O)O PHOKTTKFQUYZPI-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000000401 methanolic extract Substances 0.000 description 1
- 238000012316 non-parametric ANOVA Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- SSKVDVBQSWQEGJ-UHFFFAOYSA-N pseudohypericin Natural products C12=C(O)C=C(O)C(C(C=3C(O)=CC(O)=C4C=33)=O)=C2C3=C2C3=C4C(C)=CC(O)=C3C(=O)C3=C(O)C=C(O)C1=C32 SSKVDVBQSWQEGJ-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 230000003163 serotoninmimetic effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 229940099416 st. john's wort extract Drugs 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 125000001701 trimethoxybenzyl group Chemical group 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/647—Unsaturated compounds containing a keto groups being part of a ring having unsaturation outside the ring
- C07C49/653—Unsaturated compounds containing a keto groups being part of a ring having unsaturation outside the ring polycyclic
-
- 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
- A61K31/12—Ketones
- A61K31/122—Ketones having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/013—Esters of alcohols having the esterified hydroxy group bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/734—Ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/92—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with etherified hydroxyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Plant Substances (AREA)
- Steroid Compounds (AREA)
- Peptides Or Proteins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1998MI001312A IT1301679B1 (it) | 1998-06-10 | 1998-06-10 | Derivati dell'iperforina, loro uso e formulazioni che licontengono. |
| PCT/EP1999/003880 WO1999064388A1 (en) | 1998-06-10 | 1999-06-04 | Hyperforin derivatives, the use thereof and formulations containing them |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20006230D0 NO20006230D0 (no) | 2000-12-07 |
| NO20006230L NO20006230L (no) | 2001-02-01 |
| NO328444B1 true NO328444B1 (no) | 2010-02-22 |
Family
ID=11380210
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20006230A NO328444B1 (no) | 1998-06-10 | 2000-12-07 | Hyperforinderivat, anvendelse derav og farmasoytisk sammensetning inneholdende det |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US6656510B2 (sk) |
| EP (2) | EP1086071B1 (sk) |
| JP (1) | JP4511726B2 (sk) |
| KR (1) | KR100627933B1 (sk) |
| CN (1) | CN1246278C (sk) |
| AT (1) | ATE307103T1 (sk) |
| AU (1) | AU763889B2 (sk) |
| BR (1) | BR9910893B1 (sk) |
| CA (1) | CA2334308C (sk) |
| CZ (1) | CZ298859B6 (sk) |
| DE (1) | DE69927813T2 (sk) |
| DK (1) | DK1086071T3 (sk) |
| ES (1) | ES2249893T3 (sk) |
| HK (1) | HK1036791A1 (sk) |
| HU (1) | HUP0102226A3 (sk) |
| IL (2) | IL140151A0 (sk) |
| IT (1) | IT1301679B1 (sk) |
| MX (1) | MXPA00012177A (sk) |
| NO (1) | NO328444B1 (sk) |
| PL (1) | PL195797B1 (sk) |
| RU (1) | RU2240304C2 (sk) |
| SK (1) | SK286049B6 (sk) |
| WO (1) | WO1999064388A1 (sk) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1126882B1 (de) * | 1998-11-04 | 2009-12-30 | Dr. Willmar Schwabe GmbH & Co. KG | Stabile zubereitungen mit hyperforin |
| ITMI20020871A1 (it) * | 2002-04-23 | 2003-10-23 | Indena Spa | Derivati alogenati dell'iperforina loro uso e formulazioni che li contengono |
| ITMI20020872A1 (it) | 2002-04-23 | 2003-10-23 | Indena Spa | Derivati dell'iperforina loro uso e formulazioni che li contengono |
| US20060115556A1 (en) * | 2004-12-01 | 2006-06-01 | Foulger Sidney W | Nutritional supplement drink containing xanthone extracts |
| US20060115555A1 (en) * | 2004-12-01 | 2006-06-01 | Foulger Sidney W | Nutritional supplements containing xanthone extracts |
| BRPI0900614A2 (pt) | 2009-02-13 | 2011-06-28 | Univ Fed Do Rio Grande Do Sul Ufrgs | extrato vegetal neuroativo, composição farmacêutica compreendendo o mesmo e processo para sua produção |
| SG195210A1 (en) * | 2011-06-03 | 2013-12-30 | Harvard College | Hyperforin analogs, methods of synthesis, and uses thereof |
| ITMI20131012A1 (it) | 2013-06-19 | 2014-12-20 | Indena Spa | Derivati dell'iperforina e loro uso nella malattia di alzheimer |
| RU2676100C1 (ru) * | 2018-10-05 | 2018-12-26 | федеральное государственное автономное образовательное учреждение высшего образования "Санкт-Петербургский политехнический университет Петра Великого" (ФГАОУ ВО "СПбПУ") | Применение производных пиперазина для лечения болезни Альцгеймера и деменций альцгеймеровского типа с нарушенной внутриклеточной кальциевой сигнализацией |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2550266A (en) * | 1948-12-11 | 1951-04-24 | Swift & Co | Preservation of food products |
| DE4239959A1 (de) * | 1992-11-27 | 1994-06-01 | Schwabe Willmar Gmbh & Co | Johanniskraut-Trockenextrakt, Verfahren zu seiner Herstellung und seine Verwendung |
| DE19646977A1 (de) * | 1995-09-29 | 1998-01-15 | Schwabe Willmar Gmbh & Co | Stabiler Extrakt aus Hypericum perforatum L., Verfahren zu seiner Herstellung und pharmazeutische Zubereitungen |
| DE19714450A1 (de) * | 1997-04-08 | 1998-10-15 | Schwabe Willmar Gmbh & Co | Stabiler Extrakt aus Hypericum perforatum L., Verfahren zu seiner Herstellung und pharmazeutische Zubereitung |
| WO1999036080A1 (en) * | 1998-01-13 | 1999-07-22 | Rexall Sundown, Inc. | St. john's wort and methyl donor composition and uses thereof |
| US6224906B1 (en) * | 1999-08-31 | 2001-05-01 | Natreon Inc. | St. John's wort composition |
-
1998
- 1998-06-10 IT IT1998MI001312A patent/IT1301679B1/it active IP Right Grant
-
1999
- 1999-06-04 RU RU2000131214/04A patent/RU2240304C2/ru not_active IP Right Cessation
- 1999-06-04 MX MXPA00012177A patent/MXPA00012177A/es active IP Right Grant
- 1999-06-04 HU HU0102226A patent/HUP0102226A3/hu unknown
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