BE897473A - Nouveaux alcaloides de l'ergot de seigle leur preparation et leur utilisation comme medicaments - Google Patents

Nouveaux alcaloides de l'ergot de seigle leur preparation et leur utilisation comme medicaments Download PDF

Info

Publication number: BE897473A
Authority: BE; Belgium
Prior art keywords: compound; group; formula; addition salt; compounds
Prior art date: 1982-08-09

Application number

BE1/10847A

Other languages

English (en)

French (fr)

Original Assignee

Sandoz Sa

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

1983-08-05

Publication date

1984-02-06

1983-08-05 Application filed by Sandoz Sa filed Critical Sandoz Sa

1984-02-06 Publication of BE897473A publication Critical patent/BE897473A/fr

Links

238000002360 preparation method Methods 0.000 title claims abstract description 5
239000003814 drug Substances 0.000 title claims description 6
229960003133 ergot alkaloid Drugs 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 56
150000003839 salts Chemical class 0.000 claims abstract description 18
238000000034 method Methods 0.000 claims abstract description 17
239000002253 acid Substances 0.000 claims abstract description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 8
238000006467 substitution reaction Methods 0.000 claims abstract description 4
150000003568 thioethers Chemical class 0.000 claims abstract description 4
150000002170 ethers Chemical class 0.000 claims abstract description 3
238000011084 recovery Methods 0.000 claims abstract description 3
125000000101 thioether group Chemical group 0.000 claims abstract description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
239000000126 substance Substances 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
239000004480 active ingredient Substances 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
239000000203 mixture Substances 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
206010012289 Dementia Diseases 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
210000004556 brain Anatomy 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000000284 extract Substances 0.000 description 3
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
239000000935 antidepressant agent Substances 0.000 description 2
229940005513 antidepressants Drugs 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
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
239000003480 eluent Substances 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
230000004060 metabolic process Effects 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 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
239000011593 sulfur Substances 0.000 description 2
238000002560 therapeutic procedure Methods 0.000 description 2
230000002618 waking effect Effects 0.000 description 2
YIWGJFPJRAEKMK-UHFFFAOYSA-N 1-(2H-benzotriazol-5-yl)-3-methyl-8-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carbonyl]-1,3,8-triazaspiro[4.5]decane-2,4-dione Chemical compound CN1C(=O)N(c2ccc3n[nH]nc3c2)C2(CCN(CC2)C(=O)c2cnc(NCc3cccc(OC(F)(F)F)c3)nc2)C1=O YIWGJFPJRAEKMK-UHFFFAOYSA-N 0.000 description 1
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 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
206010019233 Headaches Diseases 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-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
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
229960004373 acetylcholine Drugs 0.000 description 1
239000013543 active substance Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229930013930 alkaloid Natural products 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
230000003042 antagnostic effect Effects 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
230000001430 anti-depressive effect Effects 0.000 description 1
239000002282 antimigraine agent Substances 0.000 description 1
229940125684 antimigraine agent Drugs 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
239000012300 argon atmosphere Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
230000005540 biological transmission Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
210000000269 carotid artery external Anatomy 0.000 description 1
230000003727 cerebral blood flow Effects 0.000 description 1
OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
229960001231 choline Drugs 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 1
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical class NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
239000006260 foam Substances 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
210000001753 habenula Anatomy 0.000 description 1
231100000869 headache Toxicity 0.000 description 1
210000001320 hippocampus Anatomy 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000011261 inert gas Substances 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
230000003340 mental effect Effects 0.000 description 1
125000005905 mesyloxy group Chemical group 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
230000001537 neural effect Effects 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
WSDQIHATCCOMLH-UHFFFAOYSA-N phenyl n-(3,5-dichlorophenyl)carbamate Chemical compound ClC1=CC(Cl)=CC(NC(=O)OC=2C=CC=CC=2)=C1 WSDQIHATCCOMLH-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
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 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)
Neurology (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Hospice & Palliative Care (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Hydrogenated Pyridines (AREA)
Plural Heterocyclic Compounds (AREA)
Pyridine Compounds (AREA)

BE1/10847A 1982-08-09 1983-08-05 Nouveaux alcaloides de l'ergot de seigle leur preparation et leur utilisation comme medicaments BE897473A (fr)

Applications Claiming Priority (1)

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.

Publications (1)

Publication Number	Publication Date
BE897473A true BE897473A (fr)	1984-02-06

Family

ID=4282273

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE1/10847A BE897473A (fr)	1982-08-09	1983-08-05	Nouveaux alcaloides de l'ergot de seigle leur preparation et leur utilisation comme medicaments

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 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 PT PT77168A patent/PT77168B/pt unknown
- 1983-08-08 SE SE8304315A patent/SE8304315L/xx not_active Application Discontinuation
- 1983-08-08 AU AU17672/83A patent/AU563736B2/en not_active Expired - Fee Related
- 1983-08-08 ES ES524815A patent/ES8502992A1/es not_active Expired
- 1983-08-08 JP JP58144843A patent/JPS5948480A/ja active Pending
- 1983-08-08 HU HU832798A patent/HU187600B/hu 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 IL IL69450A patent/IL69450A/xx unknown
- 1983-08-08 GR GR72165A patent/GR78923B/el unknown
- 1983-08-08 DK DK361983A patent/DK361983A/da unknown
- 1983-08-08 CA CA000434064A patent/CA1215972A/en not_active Expired
- 1983-08-09 PH PH29378A patent/PH20385A/en unknown
- 1983-08-09 ZA ZA835850A patent/ZA835850B/xx unknown
- 1983-08-09 IT IT22490/83A patent/IT1168961B/it active
1987
- 1987-12-30 MY MY166/87A patent/MY8700166A/xx unknown

Also Published As

Publication number	Publication date
MY8700166A (en)	1987-12-31
PH20385A (en)	1986-12-08
FR2531433A1 (fr)	1984-02-10
FI832789A0 (fi)	1983-08-02
JPS5948480A (ja)	1984-03-19
DK361983A (da)	1984-02-10
DE3327705A1 (de)	1984-02-09
IT8322490A0 (it)	1983-08-09
ES524815A0 (es)	1985-02-01
GR78923B (de)	1984-10-02
IL69450A0 (en)	1983-11-30
FI73679C (fi)	1987-11-09
DK361983D0 (da)	1983-08-08
HU187600B (en)	1986-01-28
CA1215972A (en)	1986-12-30
FR2531433B1 (fr)	1985-10-18
FI832789L (fi)	1984-02-10
FI73679B (fi)	1987-07-31
AU563736B2 (en)	1987-07-23
IT1168961B (it)	1987-05-20
IL69450A (en)	1986-10-31
ATA286383A (de)	1986-10-15
SE8304315L (sv)	1984-02-10
NL8302776A (nl)	1984-03-01
SE8304315D0 (sv)	1983-08-08
NZ205181A (en)	1986-07-11
GB2125041B (en)	1986-04-23
ES8502992A1 (es)	1985-02-01
AT383125B (de)	1987-05-25
AU1767283A (en)	1984-02-16
PT77168A (en)	1983-09-01
GB8321222D0 (en)	1983-09-07
GB2125041A (en)	1984-02-29
PT77168B (en)	1986-03-27
CH649998A5 (de)	1985-06-28
ZA835850B (en)	1985-03-27

Legal Events

Date

Code

Title

Description

1988-02-28

RE

Patent lapsed

Owner name: SANDOZ S.A.

Effective date: 19870831

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