PL205829B1 - Pochodne hiperforyny, ich zastosowanie i zawierające je preparaty - Google Patents
Pochodne hiperforyny, ich zastosowanie i zawierające je preparatyInfo
- Publication number
- PL205829B1 PL205829B1 PL371347A PL37134703A PL205829B1 PL 205829 B1 PL205829 B1 PL 205829B1 PL 371347 A PL371347 A PL 371347A PL 37134703 A PL37134703 A PL 37134703A PL 205829 B1 PL205829 B1 PL 205829B1
- Authority
- PL
- Poland
- Prior art keywords
- hyperforin
- positions
- compounds
- derivatives
- methylbut
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title description 11
- 238000009472 formulation Methods 0.000 title description 4
- 150000002448 hyperforins Chemical class 0.000 title description 3
- 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 claims abstract description 26
- 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 claims abstract description 26
- 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 claims abstract description 13
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 32
- -1 3-methyl-2-buten-1-yl Chemical group 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 150000007529 inorganic bases Chemical class 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 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 11
- 150000003839 salts Chemical class 0.000 abstract description 4
- 238000011282 treatment Methods 0.000 abstract description 4
- 208000020401 Depressive disease Diseases 0.000 abstract description 3
- 235000016709 nutrition Nutrition 0.000 abstract description 2
- 150000002148 esters Chemical class 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 23
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 14
- 101710137189 Amyloid-beta A4 protein Proteins 0.000 description 10
- 101710151993 Amyloid-beta precursor protein Proteins 0.000 description 10
- 102100022704 Amyloid-beta precursor protein Human genes 0.000 description 10
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- 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 10
- DZHSAHHDTRWUTF-SIQRNXPUSA-N amyloid-beta polypeptide 42 Chemical compound C([C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)NCC(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(O)=O)[C@@H](C)CC)C(C)C)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C(C)C)C1=CC=CC=C1 DZHSAHHDTRWUTF-SIQRNXPUSA-N 0.000 description 9
- 235000019439 ethyl acetate Nutrition 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 239000003208 petroleum Substances 0.000 description 8
- 244000141009 Hypericum perforatum Species 0.000 description 7
- 235000017309 Hypericum perforatum Nutrition 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 229910003002 lithium salt Inorganic materials 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
- 239000000284 extract Substances 0.000 description 5
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 5
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical group CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 125000000468 ketone group Chemical group 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 3
- 229910010084 LiAlH4 Inorganic materials 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 230000001430 anti-depressive effect Effects 0.000 description 3
- 239000000935 antidepressant agent Substances 0.000 description 3
- 229940005513 antidepressants Drugs 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 239000007903 gelatin capsule Substances 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- 159000000002 lithium salts Chemical class 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007832 Na2SO4 Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000013270 controlled release Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- 239000012074 organic phase 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
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 230000009182 swimming Effects 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
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 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
- 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
- 230000000949 anxiolytic effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 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
- 238000004113 cell culture Methods 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
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000003405 delayed action preparation Substances 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 229960003914 desipramine Drugs 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-O dicyclohexylazanium Chemical compound C1CCCCC1[NH2+]C1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-O 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000012048 forced swim test Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 239000000399 hydroalcoholic extract Substances 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910001411 inorganic cation Inorganic materials 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
- 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
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 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
- 239000002244 precipitate Substances 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 230000006337 proteolytic cleavage Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 238000010956 selective crystallization Methods 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 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 (1)
| 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL371347A1 PL371347A1 (en) | 2005-06-13 |
| PL205829B1 true PL205829B1 (pl) | 2010-05-31 |
Family
ID=11449767
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL371347A PL205829B1 (pl) | 2002-04-23 | 2003-04-18 | Pochodne hiperforyny, ich zastosowanie i zawierające je preparaty |
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 |
Family Cites Families (3)
| 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. |
| AU743956B2 (en) | 1998-02-13 | 2002-02-07 | Dr. Willmar Schwabe Gmbh & Co | Stable hyperforin salts, method for producing same and their use in the treatment of Alzheimer's disease |
| IT1301679B1 (it) * | 1998-06-10 | 2000-07-07 | Indena Spa | Derivati dell'iperforina, loro uso e formulazioni che licontengono. |
-
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
- 2003-04-18 PT PT03718778T patent/PT1497250E/pt unknown
- 2003-04-18 JP JP2003587762A patent/JP4315818B2/ja not_active Expired - Fee Related
- 2003-04-18 US US10/512,067 patent/US7105705B2/en not_active Ceased
- 2003-04-18 WO PCT/EP2003/004100 patent/WO2003091194A1/en not_active Ceased
- 2003-04-18 CN CNB038089319A patent/CN1290816C/zh not_active Expired - Fee Related
-
2004
- 2004-10-21 NO NO20044519A patent/NO329176B1/no not_active IP Right Cessation
- 2004-10-21 IL IL164763A patent/IL164763A/en not_active IP Right Cessation
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 |
| RU2320636C2 (ru) | 2008-03-27 |
| 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 |
| EP1497250B1 (en) | 2008-08-13 |
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