RU2320636C2 - Производные гиперфорина, их применение и содержащие их составы - Google Patents
Производные гиперфорина, их применение и содержащие их составы Download PDFInfo
- Publication number
- RU2320636C2 RU2320636C2 RU2004131210/04A RU2004131210A RU2320636C2 RU 2320636 C2 RU2320636 C2 RU 2320636C2 RU 2004131210/04 A RU2004131210/04 A RU 2004131210/04A RU 2004131210 A RU2004131210 A RU 2004131210A RU 2320636 C2 RU2320636 C2 RU 2320636C2
- Authority
- RU
- Russia
- Prior art keywords
- hyperforin
- positions
- derivatives
- compounds
- methyl
- Prior art date
Links
- 150000002448 hyperforins Chemical class 0.000 title claims abstract description 6
- 239000000203 mixture Substances 0.000 title description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- -1 3-methyl-2-butene-1-yl Chemical group 0.000 claims abstract description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims abstract description 8
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 7
- 230000001430 anti-depressive effect Effects 0.000 claims abstract description 5
- 239000003814 drug Substances 0.000 claims abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 5
- 208000020401 Depressive disease Diseases 0.000 claims abstract description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229940079593 drug Drugs 0.000 claims abstract description 4
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- MGKCAFQXBAFOSW-ACJQSPJVSA-N O=C1C(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)CC)C2=O Chemical compound O=C1C(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)CC)C2=O MGKCAFQXBAFOSW-ACJQSPJVSA-N 0.000 abstract description 2
- RIISSLSXWPTKFE-UHFFFAOYSA-N adhyperforin Natural products CCC(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 RIISSLSXWPTKFE-UHFFFAOYSA-N 0.000 abstract description 2
- XBPCUCUWBYBCDP-UHFFFAOYSA-O dicyclohexylazanium Chemical group C1CCCCC1[NH2+]C1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-O 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000007721 medicinal effect Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 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 26
- 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 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
- 239000000243 solution Substances 0.000 description 11
- 239000003208 petroleum Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 244000141009 Hypericum perforatum Species 0.000 description 6
- 235000017309 Hypericum perforatum Nutrition 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 229910003002 lithium salt Inorganic materials 0.000 description 6
- 159000000002 lithium salts Chemical class 0.000 description 6
- XVJCVVGGRAFUHV-DNSWOBEMSA-M lithium;(1r,5r,6r,7s)-6-methyl-1,3,7-tris(3-methylbutyl)-6-(4-methylpentyl)-5-(2-methylpropanoyl)-4,9-dioxobicyclo[3.3.1]non-2-en-2-olate Chemical compound [Li+].[O-]C1=C(CCC(C)C)C(=O)[C@]2(C(=O)C(C)C)[C@@](CCCC(C)C)(C)[C@@H](CCC(C)C)C[C@@]1(CCC(C)C)C2=O XVJCVVGGRAFUHV-DNSWOBEMSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 102000002659 Amyloid Precursor Protein Secretases Human genes 0.000 description 5
- 108010043324 Amyloid Precursor Protein Secretases Proteins 0.000 description 5
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 230000003595 spectral effect Effects 0.000 description 5
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 5
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical group CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- 125000000468 ketone group Chemical group 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 230000009182 swimming Effects 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 229910010082 LiAlH Inorganic materials 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000013270 controlled release Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000001828 Gelatine Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- 229940005513 antidepressants Drugs 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 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
- 238000003756 stirring Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- HCYAFALTSJYZDH-UHFFFAOYSA-N Desimpramine Chemical compound C1CC2=CC=CC=C2N(CCCNC)C2=CC=CC=C21 HCYAFALTSJYZDH-UHFFFAOYSA-N 0.000 description 1
- 206010029260 Neuroblastoma Diseases 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 230000009102 absorption Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000000049 anti-anxiety effect Effects 0.000 description 1
- 230000002555 anti-neurodegenerative effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 150000001767 cationic compounds Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229960003914 desipramine Drugs 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000002044 hexane fraction Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 125000000685 hyperforin group Chemical group 0.000 description 1
- 229910001411 inorganic cation Inorganic materials 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical class OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 230000006337 proteolytic cleavage Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009103 reabsorption Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000010956 selective crystallization Methods 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/64—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
-
- 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
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/713—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups a keto group being part of a six-membered ring
-
- 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
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/723—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic
- C07C49/727—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic a keto group being part of a condensed ring system
- C07C49/733—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic a keto group being part of a condensed ring system having two rings
-
- 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
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/743—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups having unsaturation outside the rings, e.g. humulones, lupulones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
- C07C2602/46—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing nine carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Epidemiology (AREA)
- Alternative & Traditional Medicine (AREA)
- Biotechnology (AREA)
- Botany (AREA)
- Medical Informatics (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Pain & Pain Management (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Medicines Containing Plant Substances (AREA)
- Semiconductor Lasers (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2002MI000872A ITMI20020872A1 (it) | 2002-04-23 | 2002-04-23 | Derivati dell'iperforina loro uso e formulazioni che li contengono |
| ITMI2002A000872 | 2002-04-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2004131210A RU2004131210A (ru) | 2005-04-10 |
| RU2320636C2 true RU2320636C2 (ru) | 2008-03-27 |
Family
ID=11449767
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2004131210/04A RU2320636C2 (ru) | 2002-04-23 | 2003-04-18 | Производные гиперфорина, их применение и содержащие их составы |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | USRE43280E1 (https=) |
| EP (1) | EP1497250B1 (https=) |
| JP (1) | JP4315818B2 (https=) |
| KR (1) | KR100944052B1 (https=) |
| CN (1) | CN1290816C (https=) |
| AT (1) | ATE404519T1 (https=) |
| CA (1) | CA2483205C (https=) |
| DE (1) | DE60322871D1 (https=) |
| DK (1) | DK1497250T3 (https=) |
| ES (1) | ES2311697T3 (https=) |
| IL (1) | IL164763A (https=) |
| IT (1) | ITMI20020872A1 (https=) |
| NO (1) | NO329176B1 (https=) |
| PL (1) | PL205829B1 (https=) |
| PT (1) | PT1497250E (https=) |
| RU (1) | RU2320636C2 (https=) |
| SI (1) | SI1497250T1 (https=) |
| WO (1) | WO2003091194A1 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102772461B (zh) * | 2011-05-11 | 2014-05-14 | 成都康弘药业集团股份有限公司 | 药物组合物在制备预防或治疗老年性痴呆的药物中的应用 |
| US9321713B2 (en) * | 2011-06-03 | 2016-04-26 | President And Fellows Of 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 |
| US20180071269A1 (en) | 2015-08-12 | 2018-03-15 | Tianxin Wang | Therapeutical methods, formulations and nutraceutical formulations |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999041220A1 (de) * | 1998-02-13 | 1999-08-19 | Dr. Willmar Schwabe Gmbh & Co. | Stabile hyperforin-salze, verfahren zu ihrer herstellung und verwendung zur therapie der alzheimerschen krankheit |
| WO1999064388A1 (en) * | 1998-06-10 | 1999-12-16 | Indena S.P.A. | Hyperforin derivatives, the use thereof and formulations containing them |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2162520T3 (es) * | 1998-02-13 | 2001-12-16 | Schwabe Willmar Gmbh & Co | Medicamentos basados en hiperforina y/o extractos de hiperforina. |
-
2002
- 2002-04-23 IT IT2002MI000872A patent/ITMI20020872A1/it unknown
-
2003
- 2003-04-18 PL PL371347A patent/PL205829B1/pl unknown
- 2003-04-18 RU RU2004131210/04A patent/RU2320636C2/ru not_active IP Right Cessation
- 2003-04-18 AT AT03718778T patent/ATE404519T1/de active
- 2003-04-18 ES ES03718778T patent/ES2311697T3/es not_active Expired - Lifetime
- 2003-04-18 DE DE60322871T patent/DE60322871D1/de not_active Expired - Lifetime
- 2003-04-18 CA CA2483205A patent/CA2483205C/en not_active Expired - Fee Related
- 2003-04-18 DK DK03718778T patent/DK1497250T3/da active
- 2003-04-18 SI SI200331386T patent/SI1497250T1/sl unknown
- 2003-04-18 KR KR1020047016491A patent/KR100944052B1/ko not_active Expired - Fee Related
- 2003-04-18 EP EP03718778A patent/EP1497250B1/en not_active Expired - Lifetime
- 2003-04-18 US US12/896,158 patent/USRE43280E1/en not_active Expired - Fee Related
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- 2003-04-18 US US10/512,067 patent/US7105705B2/en not_active Ceased
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2004
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999041220A1 (de) * | 1998-02-13 | 1999-08-19 | Dr. Willmar Schwabe Gmbh & Co. | Stabile hyperforin-salze, verfahren zu ihrer herstellung und verwendung zur therapie der alzheimerschen krankheit |
| WO1999064388A1 (en) * | 1998-06-10 | 1999-12-16 | Indena S.P.A. | Hyperforin derivatives, the use thereof and formulations containing them |
Also Published As
| Publication number | Publication date |
|---|---|
| HK1075654A1 (en) | 2005-12-23 |
| RU2004131210A (ru) | 2005-04-10 |
| DK1497250T3 (da) | 2008-12-01 |
| AU2003222828A1 (en) | 2003-11-10 |
| ES2311697T3 (es) | 2009-02-16 |
| USRE43280E1 (en) | 2012-03-27 |
| CN1646462A (zh) | 2005-07-27 |
| ATE404519T1 (de) | 2008-08-15 |
| CN1290816C (zh) | 2006-12-20 |
| US7105705B2 (en) | 2006-09-12 |
| IL164763A (en) | 2010-02-17 |
| NO20044519L (no) | 2004-11-02 |
| CA2483205A1 (en) | 2003-11-06 |
| EP1497250A1 (en) | 2005-01-19 |
| NO329176B1 (no) | 2010-09-06 |
| CA2483205C (en) | 2011-07-05 |
| JP2005523917A (ja) | 2005-08-11 |
| WO2003091194A1 (en) | 2003-11-06 |
| KR100944052B1 (ko) | 2010-02-24 |
| DE60322871D1 (de) | 2008-09-25 |
| KR20040111519A (ko) | 2004-12-31 |
| ITMI20020872A1 (it) | 2003-10-23 |
| ITMI20020872A0 (it) | 2002-04-23 |
| JP4315818B2 (ja) | 2009-08-19 |
| US20050165117A1 (en) | 2005-07-28 |
| SI1497250T1 (sl) | 2008-12-31 |
| PL371347A1 (en) | 2005-06-13 |
| PT1497250E (pt) | 2008-11-12 |
| IL164763A0 (en) | 2005-12-18 |
| PL205829B1 (pl) | 2010-05-31 |
| EP1497250B1 (en) | 2008-08-13 |
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| Date | Code | Title | Description |
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| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20170419 |