JPS5948480A - 麦角アルカロイド - Google Patents
麦角アルカロイドInfo
- Publication number
- JPS5948480A JPS5948480A JP58144843A JP14484383A JPS5948480A JP S5948480 A JPS5948480 A JP S5948480A JP 58144843 A JP58144843 A JP 58144843A JP 14484383 A JP14484383 A JP 14484383A JP S5948480 A JPS5948480 A JP S5948480A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- acid addition
- alkyl
- addition salt
- compounds
- 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
- 229960003133 ergot alkaloid Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 69
- 150000003839 salts Chemical class 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 241001465754 Metazoa Species 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- AWFDCTXCTHGORH-HGHGUNKESA-N 6-[4-[(6ar,9r,10ar)-5-bromo-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-carbonyl]piperazin-1-yl]-1-methylpyridin-2-one Chemical compound O=C([C@H]1CN([C@H]2[C@@H](C=3C=CC=C4NC(Br)=C(C=34)C2)C1)C)N(CC1)CCN1C1=CC=CC(=O)N1C AWFDCTXCTHGORH-HGHGUNKESA-N 0.000 claims description 3
- 206010012289 Dementia Diseases 0.000 claims description 3
- 208000012902 Nervous system disease Diseases 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 239000008024 pharmaceutical diluent Substances 0.000 claims description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 208000019695 Migraine disease Diseases 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 206010027599 migraine Diseases 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 201000000980 schizophrenia Diseases 0.000 claims description 2
- 150000003568 thioethers Chemical class 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000001939 inductive effect Effects 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 230000003639 vasoconstrictive effect Effects 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- 208000024827 Alzheimer disease Diseases 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- 206010039966 Senile dementia Diseases 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 3
- 229960004373 acetylcholine Drugs 0.000 description 3
- 239000000935 antidepressant agent Substances 0.000 description 3
- 229940005513 antidepressants Drugs 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WQADWIOXOXRPLN-UHFFFAOYSA-N 1,3-dithiane Chemical compound C1CSCSC1 WQADWIOXOXRPLN-UHFFFAOYSA-N 0.000 description 2
- CFFZDZCDUFSOFZ-UHFFFAOYSA-N 3,4-Dihydroxy-phenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C(O)=C1 CFFZDZCDUFSOFZ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- 230000001430 anti-depressive effect Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- -1 bromine Chemical class 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 230000002490 cerebral effect Effects 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
- QRMZSPFSDQBLIX-UHFFFAOYSA-N homovanillic acid Chemical compound COC1=CC(CC(O)=O)=CC=C1O QRMZSPFSDQBLIX-UHFFFAOYSA-N 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
- CXWGKAYMVASWDQ-UHFFFAOYSA-N 1,2-dithiane Chemical compound C1CCSSC1 CXWGKAYMVASWDQ-UHFFFAOYSA-N 0.000 description 1
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 description 1
- 241000282465 Canis Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 102000015554 Dopamine receptor Human genes 0.000 description 1
- 108050004812 Dopamine receptor Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- ZAGRKAFMISFKIO-UHFFFAOYSA-N Isolysergic acid Natural products C1=CC(C2=CC(CN(C2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-UHFFFAOYSA-N 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010062519 Poor quality sleep Diseases 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 206010043269 Tension headache Diseases 0.000 description 1
- 208000008548 Tension-Type Headache Diseases 0.000 description 1
- 108091000117 Tyrosine 3-Monooxygenase Proteins 0.000 description 1
- 102000048218 Tyrosine 3-monooxygenases Human genes 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 239000002282 antimigraine agent Substances 0.000 description 1
- 229940125684 antimigraine agent Drugs 0.000 description 1
- 239000003420 antiserotonin agent Substances 0.000 description 1
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 1
- 229960004046 apomorphine Drugs 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000000376 autoradiography Methods 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 210000000269 carotid artery external Anatomy 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis 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
- LOZWAPSEEHRYPG-UHFFFAOYSA-N dithiane Natural products C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 description 1
- 229960003638 dopamine Drugs 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 230000000971 hippocampal effect Effects 0.000 description 1
- 210000001320 hippocampus Anatomy 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZAGRKAFMISFKIO-QMTHXVAHSA-N lysergic acid Chemical compound C1=CC(C2=C[C@H](CN([C@@H]2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-QMTHXVAHSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000005905 mesyloxy group Chemical group 0.000 description 1
- 210000001577 neostriatum Anatomy 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229960002748 norepinephrine Drugs 0.000 description 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000002271 resection Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D457/00—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid
- C07D457/02—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid with hydrocarbon or substituted hydrocarbon radicals, attached in position 8
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH4772/82A CH649998A5 (de) | 1982-08-09 | 1982-08-09 | Ergolinderivate, ein verfahren zu ihrer herstellung und heilmittel, enthaltend diese ergolinderivate als wirkstoff. |
| CH4772/82 | 1982-08-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS5948480A true JPS5948480A (ja) | 1984-03-19 |
Family
ID=4282273
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58144843A Pending JPS5948480A (ja) | 1982-08-09 | 1983-08-08 | 麦角アルカロイド |
Country Status (23)
| Country | Link |
|---|---|
| JP (1) | JPS5948480A (en, 2012) |
| AT (1) | AT383125B (en, 2012) |
| AU (1) | AU563736B2 (en, 2012) |
| BE (1) | BE897473A (en, 2012) |
| CA (1) | CA1215972A (en, 2012) |
| CH (1) | CH649998A5 (en, 2012) |
| DE (1) | DE3327705A1 (en, 2012) |
| DK (1) | DK361983A (en, 2012) |
| ES (1) | ES8502992A1 (en, 2012) |
| FI (1) | FI73679C (en, 2012) |
| FR (1) | FR2531433B1 (en, 2012) |
| GB (1) | GB2125041B (en, 2012) |
| GR (1) | GR78923B (en, 2012) |
| HU (1) | HU187600B (en, 2012) |
| IL (1) | IL69450A (en, 2012) |
| IT (1) | IT1168961B (en, 2012) |
| MY (1) | MY8700166A (en, 2012) |
| NL (1) | NL8302776A (en, 2012) |
| NZ (1) | NZ205181A (en, 2012) |
| PH (1) | PH20385A (en, 2012) |
| PT (1) | PT77168B (en, 2012) |
| SE (1) | SE8304315L (en, 2012) |
| ZA (1) | ZA835850B (en, 2012) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4675322A (en) * | 1984-12-10 | 1987-06-23 | Eli Lilly And Company | 1-Substituted-6-n-propyl-8β-methylthio-methylergolines |
| HU193782B (en) * | 1985-06-21 | 1987-11-30 | Richter Gedeon Vegyeszet | Process for producing 2-halogeno-nicergoline derivatives and acid additional salts thereof |
| FR2589734B1 (fr) * | 1985-11-13 | 1988-09-02 | Roussel Uclaf | Utilisation de derives de l'ergoline a l'obtention d'un medicament a visee geriatrique |
| US4798834A (en) * | 1987-08-31 | 1989-01-17 | Eli Lilly And Company | Optionally substituted (3β-9,10-didehydro-2,3-dihydro ergoline as serotonergic function enhancement |
| DE3913756A1 (de) * | 1989-04-21 | 1990-10-25 | Schering Ag | 8(beta)-substituierte ergoline, verfahren zu ihrer herstellung und ihre verwendung |
| DE10212564B4 (de) * | 2002-03-12 | 2007-04-19 | Neurobiotec Gmbh | 1-Allyl-ergotalkaloid-Derivate und ihre Verwendung zur Prophylaxe und Therapie von Migräne |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE41533B1 (en) * | 1974-03-14 | 1980-01-30 | Sandoz Ltd | Thiomethyl ergolene derivatives |
| US3901894A (en) * | 1974-06-06 | 1975-08-26 | Lilly Co Eli | 8-thiomethylergolines |
| US3959288A (en) * | 1974-12-13 | 1976-05-25 | Eli Lilly And Company | 8-Oxymethylergolines and process therefor |
| US4166182A (en) * | 1978-02-08 | 1979-08-28 | Eli Lilly And Company | 6-n-propyl-8-methoxymethyl or methylmercaptomethylergolines and related compounds |
| US4382940A (en) * | 1979-12-06 | 1983-05-10 | Farmitalia Carlo Erba S.P.A. | Ercoline derivatives and therapeutic compositions having CNS affecting activity |
-
1982
- 1982-08-09 CH CH4772/82A patent/CH649998A5/de not_active IP Right Cessation
-
1983
- 1983-08-01 DE DE19833327705 patent/DE3327705A1/de not_active Withdrawn
- 1983-08-02 FI FI832789A patent/FI73679C/fi not_active IP Right Cessation
- 1983-08-04 FR FR8313018A patent/FR2531433B1/fr not_active Expired
- 1983-08-05 NL NL8302776A patent/NL8302776A/nl not_active Application Discontinuation
- 1983-08-05 GB GB08321222A patent/GB2125041B/en not_active Expired
- 1983-08-05 BE BE1/10847A patent/BE897473A/fr not_active IP Right Cessation
- 1983-08-08 JP JP58144843A patent/JPS5948480A/ja active Pending
- 1983-08-08 AU AU17672/83A patent/AU563736B2/en not_active Expired - Fee Related
- 1983-08-08 DK DK361983A patent/DK361983A/da unknown
- 1983-08-08 PT PT77168A patent/PT77168B/pt unknown
- 1983-08-08 ES ES524815A patent/ES8502992A1/es not_active Expired
- 1983-08-08 SE SE8304315A patent/SE8304315L/xx not_active Application Discontinuation
- 1983-08-08 GR GR72165A patent/GR78923B/el unknown
- 1983-08-08 AT AT0286383A patent/AT383125B/de not_active IP Right Cessation
- 1983-08-08 NZ NZ205181A patent/NZ205181A/en unknown
- 1983-08-08 CA CA000434064A patent/CA1215972A/en not_active Expired
- 1983-08-08 HU HU832798A patent/HU187600B/hu unknown
- 1983-08-08 IL IL69450A patent/IL69450A/xx unknown
- 1983-08-09 ZA ZA835850A patent/ZA835850B/xx unknown
- 1983-08-09 IT IT22490/83A patent/IT1168961B/it active
- 1983-08-09 PH PH29378A patent/PH20385A/en unknown
-
1987
- 1987-12-30 MY MY166/87A patent/MY8700166A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2531433A1 (fr) | 1984-02-10 |
| SE8304315L (sv) | 1984-02-10 |
| IL69450A0 (en) | 1983-11-30 |
| DK361983D0 (da) | 1983-08-08 |
| HU187600B (en) | 1986-01-28 |
| NL8302776A (nl) | 1984-03-01 |
| GB8321222D0 (en) | 1983-09-07 |
| MY8700166A (en) | 1987-12-31 |
| IT1168961B (it) | 1987-05-20 |
| FI73679C (fi) | 1987-11-09 |
| AU563736B2 (en) | 1987-07-23 |
| ZA835850B (en) | 1985-03-27 |
| PH20385A (en) | 1986-12-08 |
| DK361983A (da) | 1984-02-10 |
| PT77168B (en) | 1986-03-27 |
| PT77168A (en) | 1983-09-01 |
| FI832789A0 (fi) | 1983-08-02 |
| DE3327705A1 (de) | 1984-02-09 |
| ATA286383A (de) | 1986-10-15 |
| FR2531433B1 (fr) | 1985-10-18 |
| ES524815A0 (es) | 1985-02-01 |
| AU1767283A (en) | 1984-02-16 |
| CA1215972A (en) | 1986-12-30 |
| IT8322490A0 (it) | 1983-08-09 |
| BE897473A (fr) | 1984-02-06 |
| AT383125B (de) | 1987-05-25 |
| CH649998A5 (de) | 1985-06-28 |
| GR78923B (en, 2012) | 1984-10-02 |
| GB2125041B (en) | 1986-04-23 |
| FI73679B (fi) | 1987-07-31 |
| SE8304315D0 (sv) | 1983-08-08 |
| NZ205181A (en) | 1986-07-11 |
| IL69450A (en) | 1986-10-31 |
| GB2125041A (en) | 1984-02-29 |
| FI832789L (fi) | 1984-02-10 |
| ES8502992A1 (es) | 1985-02-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6379649B1 (en) | Imidazo(1,2-a)pyridines as peripheral benzodiazepine receptor binding agents | |
| CZ288944B6 (cs) | Derivát 5H-thiazolo[3,2-a]pyrimidinu, způsob jeho přípravy, meziprodukt pro jeho přípravu a farmaceutický prostředek, který ho obsahuje | |
| PT1354884E (pt) | Composto de ciclopenta (d) pirazolo [1,5-a] piramida como antagonista de receptor de crf | |
| CN113717167B (zh) | 并环化合物及其制备方法、药物组合物和应用 | |
| US8546388B2 (en) | Heterocyclic TRPV1 receptor ligands | |
| HUT65947A (en) | Imidazo-pyridine - derivatives with paf/h1 antagonist activity and pharmaceutical compositions containing them and process for the production thereof | |
| RU2165420C2 (ru) | 1,2,5-тиадиазольные производные индолилалкил-пиримидинил-пиперазинов и фармацевтическая композиция на их основе | |
| US3843663A (en) | 1,8-naphthyridine compounds | |
| JPS5948480A (ja) | 麦角アルカロイド | |
| CN113698388B (zh) | 6-氧代-1,6-二氢吡啶类衍生物、其制备方法及其在医药上的应用 | |
| JPS60174783A (ja) | 新規８α‐アシルアミノエルゴリン類 | |
| JPH07505394A (ja) | 橋渡しビスアリールカルビノール誘導体，組成物および使用法 | |
| JPS61100579A (ja) | ピリジン誘導体 | |
| WO2022171126A1 (zh) | 作为Wee-1抑制剂的稠环化合物 | |
| JPS61158980A (ja) | ８α‐アシルアミノエルゴリン類、その製法および医薬組成物 | |
| US4032640A (en) | 4H-Benzo[4,5]cyclohepta[1,2-b]thiophenes | |
| DE69903627T2 (de) | Tetrahydroisochinolinderivate als modulatoren von dopamin d3 rezeptoren | |
| WO1996021662A1 (en) | THE USE OF HETEROCYCLIC COMPOUNDS AS ANTIOXIDANTS, RADICAL SCAVENGERS, Fe2+ COMPLEXING AGENTS, TISSUE- AND/OR NEUROPROTECTANTS | |
| JPH03294277A (ja) | ピペリジン誘導体 | |
| PT99280B (pt) | Processo de preparacao de derivados do indolo e de composicoes farmaceuticas | |
| JPS59184162A (ja) | キノリン誘導体、その製造法及び該化合物を含有する、５―ヒドロキシトリプタミン桔抗質として使用する医薬組成物 | |
| EP0119541A1 (en) | Substituted 4,10-dihydro-10-oxothieno-benzoxepins, a process for their preparation and their use as medicaments | |
| JPH01242574A (ja) | 含窒素縮合環を有するピペリジン及びピペラジン誘導体、その製造方法並びにそれを含む薬学的組成物 | |
| JPH0495071A (ja) | カルバミン酸誘導体 | |
| JP3047112B2 (ja) | 置換アリールアミン類およびヘテロアリールアミン類、それらの製造方法、およびそれらの薬理組成物 |