CN1125725A - 一类海克林碱衍生物及它的用途 - Google Patents
一类海克林碱衍生物及它的用途 Download PDFInfo
- Publication number
- CN1125725A CN1125725A CN94114057A CN94114057A CN1125725A CN 1125725 A CN1125725 A CN 1125725A CN 94114057 A CN94114057 A CN 94114057A CN 94114057 A CN94114057 A CN 94114057A CN 1125725 A CN1125725 A CN 1125725A
- Authority
- CN
- China
- Prior art keywords
- derivative
- selagine
- physiological saline
- haikelin
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000003513 alkali Substances 0.000 title claims abstract description 8
- 241001597008 Nomeidae Species 0.000 title claims description 4
- 239000002904 solvent Substances 0.000 claims abstract description 6
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims abstract 2
- ZRJBHWIHUMBLCN-YQEJDHNASA-N huperzine A Chemical compound N1C(=O)C=CC2=C1C[C@H]1\C(=C/C)[C@]2(N)CC(C)=C1 ZRJBHWIHUMBLCN-YQEJDHNASA-N 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 15
- ZRJBHWIHUMBLCN-UHFFFAOYSA-N Shuangyiping Natural products N1C(=O)C=CC2=C1CC1C(=CC)C2(N)CC(C)=C1 ZRJBHWIHUMBLCN-UHFFFAOYSA-N 0.000 claims description 11
- ZRJBHWIHUMBLCN-BMIGLBTASA-N rac-huperzine A Natural products N1C(=O)C=CC2=C1C[C@@H]1C(=CC)[C@@]2(N)CC(C)=C1 ZRJBHWIHUMBLCN-BMIGLBTASA-N 0.000 claims description 11
- APLHEOBEIBHCHW-YQEJDHNASA-N Selagine Natural products O=C1NC2=C([C@]3(N)/C(=C/C)/[C@@H](CC(C)=C3)C2)C=C1 APLHEOBEIBHCHW-YQEJDHNASA-N 0.000 claims description 10
- -1 substituted-phenyl Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 230000001713 cholinergic effect Effects 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 150000001263 acyl chlorides Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 claims description 2
- 230000007074 memory dysfunction Effects 0.000 claims description 2
- 206010028417 myasthenia gravis Diseases 0.000 claims description 2
- 102000003914 Cholinesterases Human genes 0.000 claims 1
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- 229940048961 cholinesterase Drugs 0.000 claims 1
- 230000000994 depressogenic effect Effects 0.000 claims 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- 108090000371 Esterases Proteins 0.000 abstract 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 abstract 1
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- 238000006482 condensation reaction Methods 0.000 abstract 1
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- 231100000053 low toxicity Toxicity 0.000 abstract 1
- 239000002504 physiological saline solution Substances 0.000 description 12
- 229930000680 A04AD01 - Scopolamine Natural products 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
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- STECJAGHUSJQJN-UHFFFAOYSA-N N-Methyl-scopolamin Natural products C1C(C2C3O2)N(C)C3CC1OC(=O)C(CO)C1=CC=CC=C1 STECJAGHUSJQJN-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- STECJAGHUSJQJN-FWXGHANASA-N scopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-FWXGHANASA-N 0.000 description 10
- 229960002646 scopolamine Drugs 0.000 description 10
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 102100033639 Acetylcholinesterase Human genes 0.000 description 7
- 108010022752 Acetylcholinesterase Proteins 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 229940022698 acetylcholinesterase Drugs 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 241000699666 Mus <mouse, genus> Species 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- 239000000544 cholinesterase inhibitor Substances 0.000 description 4
- 230000015654 memory Effects 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 102100032404 Cholinesterase Human genes 0.000 description 3
- 101710083761 Cholinesterase Proteins 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229930013930 alkaloid Natural products 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 229960004756 ethanol Drugs 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 230000000452 restraining effect Effects 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241001113926 Gelsemium Species 0.000 description 2
- ZQPQGKQTIZYFEF-WCVJEAGWSA-N Huperzine Natural products C1([C@H]2[C@H](O)C(=O)N[C@H]2[C@@H](O)C=2C=CC=CC=2)=CC=CC=C1 ZQPQGKQTIZYFEF-WCVJEAGWSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000208278 Hyoscyamus Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- PIJVFDBKTWXHHD-UHFFFAOYSA-N Physostigmine Natural products C12=CC(OC(=O)NC)=CC=C2N(C)C2C1(C)CCN2C PIJVFDBKTWXHHD-UHFFFAOYSA-N 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 150000003797 alkaloid derivatives Chemical class 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- 238000004737 colorimetric analysis Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 210000003027 ear inner Anatomy 0.000 description 2
- ASUTZQLVASHGKV-JDFRZJQESA-N galanthamine Chemical compound O1C(=C23)C(OC)=CC=C2CN(C)CC[C@]23[C@@H]1C[C@@H](O)C=C2 ASUTZQLVASHGKV-JDFRZJQESA-N 0.000 description 2
- 241000411851 herbal medicine Species 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229960001697 physostigmine Drugs 0.000 description 2
- PIJVFDBKTWXHHD-HIFRSBDPSA-N physostigmine Chemical compound C12=CC(OC(=O)NC)=CC=C2N(C)[C@@H]2[C@@]1(C)CCN2C PIJVFDBKTWXHHD-HIFRSBDPSA-N 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 235000014347 soups Nutrition 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000012549 training Methods 0.000 description 2
- 230000003936 working memory Effects 0.000 description 2
- NTBLZMAMTZXLBP-UHFFFAOYSA-M 2-acetylsulfanylethyl(trimethyl)azanium;iodide Chemical compound [I-].CC(=O)SCC[N+](C)(C)C NTBLZMAMTZXLBP-UHFFFAOYSA-M 0.000 description 1
- IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 1
- 208000014644 Brain disease Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- ZRJBHWIHUMBLCN-SEQYCRGISA-N Huperzine A Natural products N1C(=O)C=CC2=C1C[C@H]1/C(=C/C)[C@]2(N)CC(C)=C1 ZRJBHWIHUMBLCN-SEQYCRGISA-N 0.000 description 1
- 101100022875 Mus musculus Meox1 gene Proteins 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 239000004141 Sodium laurylsulphate Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
- 238000011047 acute toxicity test Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 description 1
- 239000004913 cyclooctene Substances 0.000 description 1
- 238000013016 damping Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000003412 degenerative effect Effects 0.000 description 1
- 229960000935 dehydrated alcohol Drugs 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000009189 diving Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 210000003617 erythrocyte membrane Anatomy 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 229960003980 galantamine Drugs 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 206010027175 memory impairment Diseases 0.000 description 1
- 101150029117 meox2 gene Proteins 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- RABUZJZUBFMWSH-UHFFFAOYSA-N sulfane;hydroiodide Chemical compound [SH3+].[I-] RABUZJZUBFMWSH-UHFFFAOYSA-N 0.000 description 1
- 229940074412 sulfur iodide Drugs 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular 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
- A61P25/28—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
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/22—Bridged ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN94114057A CN1125725A (zh) | 1994-12-28 | 1994-12-28 | 一类海克林碱衍生物及它的用途 |
| PT95941572T PT806416E (pt) | 1994-12-28 | 1995-12-26 | Derivados de huperzina a sua preparacao e utilizacao |
| US09/799,127 USRE38460E1 (en) | 1994-12-28 | 1995-12-26 | Huperzine A derivatives, their preparation and their use |
| DK95941572T DK0806416T3 (da) | 1994-12-28 | 1995-12-26 | Huperzinderivater, deres fremstilling og anvendelse |
| JP52010296A JP3545416B2 (ja) | 1994-12-28 | 1995-12-26 | フペルジンａ誘導体、その製造およびその使用 |
| EP95941572A EP0806416B1 (en) | 1994-12-28 | 1995-12-26 | Huperzine a derivatives, their preparation and their use |
| AT95941572T ATE239708T1 (de) | 1994-12-28 | 1995-12-26 | Huperzin-derivate, ihre herstellung und ihre verwendung |
| DE69530706T DE69530706T2 (de) | 1994-12-28 | 1995-12-26 | Huperzin-derivate, ihre herstellung und ihre verwendung |
| AU42966/96A AU4296696A (en) | 1994-12-28 | 1995-12-26 | Huperzine a derivatives, their preparation and their use |
| ES95941572T ES2199259T3 (es) | 1994-12-28 | 1995-12-26 | Derivados de huperzina, su preparacion y su utilizacion. |
| US08/860,524 US5929084A (en) | 1994-12-28 | 1995-12-26 | Huperzine A derivatives, their preparation and their use |
| PCT/CN1995/000100 WO1996020176A1 (en) | 1994-12-28 | 1995-12-26 | Huperzine a derivatives, their preparation and their use |
| JP2003148129A JP4105592B2 (ja) | 1994-12-28 | 2003-05-26 | フペルジンａ誘導体、その製造およびその使用 |
| JP2007174592A JP2007246545A (ja) | 1994-12-28 | 2007-07-02 | フペルジンａ誘導体、その製造およびその使用 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN94114057A CN1125725A (zh) | 1994-12-28 | 1994-12-28 | 一类海克林碱衍生物及它的用途 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1125725A true CN1125725A (zh) | 1996-07-03 |
Family
ID=5037011
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN94114057A Pending CN1125725A (zh) | 1994-12-28 | 1994-12-28 | 一类海克林碱衍生物及它的用途 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US5929084A (OSRAM) |
| EP (1) | EP0806416B1 (OSRAM) |
| JP (3) | JP3545416B2 (OSRAM) |
| CN (1) | CN1125725A (OSRAM) |
| AT (1) | ATE239708T1 (OSRAM) |
| AU (1) | AU4296696A (OSRAM) |
| DE (1) | DE69530706T2 (OSRAM) |
| DK (1) | DK0806416T3 (OSRAM) |
| ES (1) | ES2199259T3 (OSRAM) |
| PT (1) | PT806416E (OSRAM) |
| WO (1) | WO1996020176A1 (OSRAM) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1308312C (zh) * | 2003-11-13 | 2007-04-04 | 中国科学院上海药物研究所 | 石杉碱乙双分子和双功能团衍生物、制备方法及它的用途 |
| CN100398093C (zh) * | 2003-03-14 | 2008-07-02 | 德比欧药物研究有限公司 | 皮下给药系统、其制备方法及其治疗胆碱能缺乏障碍的用途 |
| CN100528844C (zh) * | 2007-04-20 | 2009-08-19 | 中国科学院昆明植物研究所 | 石杉碱甲衍生物,其制备方法和其应用 |
| CN101797223B (zh) * | 2009-02-06 | 2012-05-23 | 上海交通大学医学院 | 石杉碱甲眼用制剂及其应用 |
| CN116925039A (zh) * | 2023-07-18 | 2023-10-24 | 陕西中药研究所(陕西医药信息中心) | 一种n-(3,5,6-三甲基吡嗪-2-亚甲基)-石杉碱甲及其合成方法和应用 |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100210590A1 (en) * | 1995-09-27 | 2010-08-19 | Northwestern University | Compositions and treatments for seizure-related disorders |
| NL1009437C2 (nl) * | 1998-06-18 | 1999-12-21 | Xenobiosis | Extractiewerkwijze. |
| EP1604653A1 (en) | 1998-09-30 | 2005-12-14 | Takeda Pharmaceutical Company Limited | Acetylcholinesterase inhibitors for improving excretory potency of urinary bladder |
| US6159986A (en) * | 1999-11-02 | 2000-12-12 | Altman; David A. | Compounds and therapy for resisting memory loss in humans |
| US6436972B1 (en) | 2000-04-10 | 2002-08-20 | Dalhousie University | Pyridones and their use as modulators of serine hydrolase enzymes |
| EP1283902A4 (en) * | 2000-05-05 | 2007-05-02 | Us Army Medical Res And Materi | ANALYSIS FOR THE DETECTION, MEASUREMENT AND CONTROL OF PROTEIN ACTIVITIES AND CONCENTRATIONS AND METHODS OF USE |
| US6369052B1 (en) | 2000-08-07 | 2002-04-09 | Georgetown University | Combination of huperzine and nicotinic compounds as a neuroprotective agent |
| KR100390777B1 (ko) * | 2000-12-19 | 2003-07-10 | 한국화학연구원 | 피리돈 유도체의 제조방법 |
| DE10144041B9 (de) * | 2001-09-07 | 2012-07-26 | Leica Mikrosysteme Gmbh | Gerät zum selbsttätigen Zuführen von Objektträgern zu einem Eindeckautomaten |
| PL1603532T3 (pl) * | 2003-03-14 | 2009-02-27 | Debio Rech Pharmaceutique S A | System dostarczania podskórnego, sposób jego wytwarzania oraz jego zastosowanie do leczenia zaburzeń z deficytem cholinergicznym |
| US20050222123A1 (en) | 2004-01-27 | 2005-10-06 | North Shore-Long Island Jewish Research Institute | Cholinesterase inhibitors for treating inflammation |
| CA2589102C (en) * | 2004-11-02 | 2013-08-13 | Northwestern University | Pyridazine compounds and methods for using the compounds to treat inflammatory diseases |
| EP3056200B1 (en) | 2005-05-23 | 2023-09-06 | President and Fellows of Harvard College | Huperzine for use in treating seizure |
| US20070179123A1 (en) * | 2005-11-08 | 2007-08-02 | Chiang Peter K | Methods and compositions for treating diseases associated with pathogenic proteins |
| EP2015750A2 (en) * | 2006-04-28 | 2009-01-21 | Northwestern University | Compositions and treatments using pyridazine compounds and cholinesterase inhibitors |
| US8097726B2 (en) * | 2006-05-17 | 2012-01-17 | Industrial Technology Research Institute | Huperzine a compound for treatment of alzheimer's disease |
| WO2008006286A1 (fr) * | 2006-07-05 | 2008-01-17 | Tianjin Hemay Bio-Tech Co. Ltd | Dérivés analgésiques 5,9 - méthanocyclo-octa (b) pyridine - 2 (1h) - one, leur procédé de préparation et leur utilisation |
| TWI404531B (zh) * | 2007-05-17 | 2013-08-11 | Ind Tech Res Inst | 石杉鹼甲化合物及包含此化合物之醫藥組合物 |
| WO2010028134A2 (en) * | 2008-09-04 | 2010-03-11 | President And Fellows Of Harvard College | Treatment of neurological disorders using huperzine |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5177082A (en) * | 1985-11-05 | 1993-01-05 | Yu Chao Mei | Huperzines and analogs |
| US4968672A (en) * | 1987-01-02 | 1990-11-06 | The United States Of America As Represented By The Department Of Health And Human Services | Adenosine receptor prodrugs |
| US4929731A (en) * | 1989-02-21 | 1990-05-29 | University Of Pittsburgh | Method for the synthesis of huperzine A and analogs thereof and compounds useful therein |
| US5104880A (en) * | 1991-05-01 | 1992-04-14 | Mayo Foundation For Medical Education And Research | Huperzine a analogs as acetylcholinesterase inhibitors |
| US5684018A (en) * | 1994-12-13 | 1997-11-04 | Merck & Co., Inc. | Acyloxyisopropyl carbamates as prodrugs for amine drugs |
-
1994
- 1994-12-28 CN CN94114057A patent/CN1125725A/zh active Pending
-
1995
- 1995-12-26 EP EP95941572A patent/EP0806416B1/en not_active Expired - Lifetime
- 1995-12-26 AT AT95941572T patent/ATE239708T1/de not_active IP Right Cessation
- 1995-12-26 JP JP52010296A patent/JP3545416B2/ja not_active Expired - Fee Related
- 1995-12-26 DE DE69530706T patent/DE69530706T2/de not_active Expired - Fee Related
- 1995-12-26 PT PT95941572T patent/PT806416E/pt unknown
- 1995-12-26 US US08/860,524 patent/US5929084A/en not_active Ceased
- 1995-12-26 ES ES95941572T patent/ES2199259T3/es not_active Expired - Lifetime
- 1995-12-26 AU AU42966/96A patent/AU4296696A/en not_active Abandoned
- 1995-12-26 WO PCT/CN1995/000100 patent/WO1996020176A1/zh not_active Ceased
- 1995-12-26 DK DK95941572T patent/DK0806416T3/da active
-
2003
- 2003-05-26 JP JP2003148129A patent/JP4105592B2/ja not_active Expired - Fee Related
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2007
- 2007-07-02 JP JP2007174592A patent/JP2007246545A/ja active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100398093C (zh) * | 2003-03-14 | 2008-07-02 | 德比欧药物研究有限公司 | 皮下给药系统、其制备方法及其治疗胆碱能缺乏障碍的用途 |
| CN1308312C (zh) * | 2003-11-13 | 2007-04-04 | 中国科学院上海药物研究所 | 石杉碱乙双分子和双功能团衍生物、制备方法及它的用途 |
| CN100528844C (zh) * | 2007-04-20 | 2009-08-19 | 中国科学院昆明植物研究所 | 石杉碱甲衍生物,其制备方法和其应用 |
| CN101797223B (zh) * | 2009-02-06 | 2012-05-23 | 上海交通大学医学院 | 石杉碱甲眼用制剂及其应用 |
| CN116925039A (zh) * | 2023-07-18 | 2023-10-24 | 陕西中药研究所(陕西医药信息中心) | 一种n-(3,5,6-三甲基吡嗪-2-亚甲基)-石杉碱甲及其合成方法和应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE69530706D1 (de) | 2003-06-12 |
| JP3545416B2 (ja) | 2004-07-21 |
| WO1996020176A1 (en) | 1996-07-04 |
| DE69530706T2 (de) | 2004-03-25 |
| ATE239708T1 (de) | 2003-05-15 |
| EP0806416A4 (en) | 1998-04-15 |
| PT806416E (pt) | 2003-09-30 |
| AU4296696A (en) | 1996-07-19 |
| DK0806416T3 (da) | 2003-09-01 |
| EP0806416B1 (en) | 2003-05-07 |
| JP2007246545A (ja) | 2007-09-27 |
| JP4105592B2 (ja) | 2008-06-25 |
| ES2199259T3 (es) | 2004-02-16 |
| JPH10511651A (ja) | 1998-11-10 |
| EP0806416A1 (en) | 1997-11-12 |
| US5929084A (en) | 1999-07-27 |
| JP2003306481A (ja) | 2003-10-28 |
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