JPS5948480A - 麦角アルカロイド - Google Patents

麦角アルカロイド

Info

Publication number: JPS5948480A
Authority: JP; Japan
Prior art keywords: compound; acid addition; alkyl; addition salt; compounds
Prior art date: 1982-08-09
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

Application number

JP58144843A

Other languages

English (en)

Japanese (ja)

Inventor

ペ−タ−・グル

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sandoz AG

Original Assignee

Sandoz AG

Priority date (The priority date 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 date listed.)

1982-08-09

Filing date

1983-08-08

Publication date

1984-03-19

1983-08-08 Application filed by Sandoz AG filed Critical Sandoz AG

1984-03-19 Publication of JPS5948480A publication Critical patent/JPS5948480A/ja

Status Pending legal-status Critical Current

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)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Hospice & Palliative Care (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)
Pyridine Compounds (AREA)
Hydrogenated Pyridines (AREA)

JP58144843A 1982-08-09 1983-08-08 麦角アルカロイド Pending JPS5948480A (ja)

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 (de)
AT (1)	AT383125B (de)
AU (1)	AU563736B2 (de)
BE (1)	BE897473A (de)
CA (1)	CA1215972A (de)
CH (1)	CH649998A5 (de)
DE (1)	DE3327705A1 (de)
DK (1)	DK361983A (de)
ES (1)	ES8502992A1 (de)
FI (1)	FI73679C (de)
FR (1)	FR2531433B1 (de)
GB (1)	GB2125041B (de)
GR (1)	GR78923B (de)
HU (1)	HU187600B (de)
IL (1)	IL69450A (de)
IT (1)	IT1168961B (de)
MY (1)	MY8700166A (de)
NL (1)	NL8302776A (de)
NZ (1)	NZ205181A (de)
PH (1)	PH20385A (de)
PT (1)	PT77168B (de)
SE (1)	SE8304315L (de)
ZA (1)	ZA835850B (de)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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 GB GB08321222A patent/GB2125041B/en not_active Expired
- 1983-08-05 NL NL8302776A patent/NL8302776A/nl not_active Application Discontinuation
- 1983-08-05 BE BE1/10847A patent/BE897473A/fr not_active IP Right Cessation
- 1983-08-08 ES ES524815A patent/ES8502992A1/es not_active Expired
- 1983-08-08 CA CA000434064A patent/CA1215972A/en not_active Expired
- 1983-08-08 GR GR72165A patent/GR78923B/el unknown
- 1983-08-08 JP JP58144843A patent/JPS5948480A/ja active Pending
- 1983-08-08 NZ NZ205181A patent/NZ205181A/en unknown
- 1983-08-08 DK DK361983A patent/DK361983A/da unknown
- 1983-08-08 AU AU17672/83A patent/AU563736B2/en not_active Expired - Fee Related
- 1983-08-08 HU HU832798A patent/HU187600B/hu unknown
- 1983-08-08 SE SE8304315A patent/SE8304315L/xx not_active Application Discontinuation
- 1983-08-08 PT PT77168A patent/PT77168B/pt unknown
- 1983-08-08 IL IL69450A patent/IL69450A/xx unknown
- 1983-08-08 AT AT0286383A patent/AT383125B/de not_active IP Right Cessation
- 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
FI73679B (fi)	1987-07-31
FR2531433B1 (fr)	1985-10-18
NZ205181A (en)	1986-07-11
FI73679C (fi)	1987-11-09
GR78923B (de)	1984-10-02
DK361983D0 (da)	1983-08-08
HU187600B (en)	1986-01-28
FI832789A0 (fi)	1983-08-02
GB2125041B (en)	1986-04-23
CH649998A5 (de)	1985-06-28
IT8322490A0 (it)	1983-08-09
GB8321222D0 (en)	1983-09-07
PT77168B (en)	1986-03-27
DK361983A (da)	1984-02-10
IT1168961B (it)	1987-05-20
GB2125041A (en)	1984-02-29
PT77168A (en)	1983-09-01
AU1767283A (en)	1984-02-16
ZA835850B (en)	1985-03-27
SE8304315L (sv)	1984-02-10
FI832789L (fi)	1984-02-10
IL69450A (en)	1986-10-31
SE8304315D0 (sv)	1983-08-08
CA1215972A (en)	1986-12-30
NL8302776A (nl)	1984-03-01
DE3327705A1 (de)	1984-02-09
ATA286383A (de)	1986-10-15
IL69450A0 (en)	1983-11-30
AT383125B (de)	1987-05-25
PH20385A (en)	1986-12-08
ES524815A0 (es)	1985-02-01
AU563736B2 (en)	1987-07-23
MY8700166A (en)	1987-12-31
ES8502992A1 (es)	1985-02-01
BE897473A (fr)	1984-02-06

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