EP0000479B1 - 1-Pipérazinyl-4H-s-triazolo (3,4-c)thiéno (2,3-e)1,4-diazépines, procédé pour leur préparation et médicaments les contenant - Google Patents
1-Pipérazinyl-4H-s-triazolo (3,4-c)thiéno (2,3-e)1,4-diazépines, procédé pour leur préparation et médicaments les contenant Download PDFInfo
- Publication number
- EP0000479B1 EP0000479B1 EP78100263A EP78100263A EP0000479B1 EP 0000479 B1 EP0000479 B1 EP 0000479B1 EP 78100263 A EP78100263 A EP 78100263A EP 78100263 A EP78100263 A EP 78100263A EP 0000479 B1 EP0000479 B1 EP 0000479B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- thieno
- triazolo
- formula
- piperazinyl
- hydroxy
- 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.)
- Expired
Links
- 0 CC1=*N=C(COC(C2=CC(*)=S*2)c(cccc2)c2Cl)C1 Chemical compound CC1=*N=C(COC(C2=CC(*)=S*2)c(cccc2)c2Cl)C1 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
Definitions
- Thieno-triazolo-diazepines are known to be anxiolytic, muscle relaxant and anticonvulsant. These are compounds which are attached to the triazole ring, for example by alkyl (DT-OS 2405682), cycloalkyl (DBP 2435041), an oxygen-containing 5- or 6-membered ring (DT-AS 2445430) or a nitrogen or sulfur-containing 5- or 6-membered ring (DT-OS 2460776) are substituted.
- 8-bromo-6- (o-chlorophenyl) -1- [N- (2-hydroxyethyl) piperazinyl] -4H-s-triazolo [3,4c] thieno [2,3e] 1,4-diazepine Salts form and, in this form, have a water solubility of 0.5% which is important for the diazepine substance class. This allows parenteral use of the compound, e.g. in the anesthetic preparation.
- 8-bromo-6- (o-chlorophenyl) -1-methyl-4H-s-triazalo [3,4c] thieno [2,3e] 1,4-diazepine extends deep and REM sleep and impresses to a much greater extent the engine coordination.
- reaction of compounds of general formula II with a piperazine of formula 111 is carried out either without a solvent or in higher-boiling solvents such as benzene, toluene, dioxane, tetrahydrofuran, chlorinated hydrocarbons such as carbon tetrachloride or methylene chloride, preferably at the boiling point of the solvent used.
- the reaction time depends on the starting material used and can range from a few minutes to several hours.
- dehydrogenation of compounds of the general formula IV is carried out using suitable dehydrogenation agents such as, for example, halogens or else compounds of the higher oxidation states of chromium or manganese, for example a chromate, a bichromate or a permanganate.
- suitable dehydrogenation agents such as, for example, halogens or else compounds of the higher oxidation states of chromium or manganese, for example a chromate, a bichromate or a permanganate.
- Chlorinated hydrocarbons such as chloroform or methylene chloride may be mentioned as suitable solvents for the reaction with a halogen.
- the oxidation with the mentioned chromium or manganese compounds takes place in solvents such as acetone, tetrahydrofuran or dioxane.
- the reaction temperature is generally between 0 ° C and the boiling point of the solvent used.
- the 8-bromo-6- (o-chlorophenyl) -1- [N- (2-hydroxyethyl) piperazinyl] -4H-s-triazolo [3,4c] thieno no [2,3e] forms 1,4-diazepine stable water-soluble salts.
- Suitable for salt formation are all acids which form physiologically acceptable acid addition salts such as hydrohalic acids, sulfuric acid, phosphoric acid, nitric acid, cyclohexylsulfamic acid, citric acid, tartaric acid, ascorbic acid, maleic acid, formic acid, salicylic acid, methane or toluenesulfonic acid.
- the starting compounds of the general formula II are known from the literature.
- Starting compounds of the general formula IV are obtained by reacting a compound of the formula in the Hal means a halogen atom, with a piperazine derivative of the formula 111 under the conditions given under a) and then replacing the ring oxygen atom with a nitrogen atom, as described, for example, in German application P 2531678.
- the single dose of the substances according to the invention is 0.05 to 50, preferably 0.1 to 25 mg (oral) and 5 to 150 mg as a daily dose.
- the compounds obtainable according to the invention can be used alone or in combination with other active substances according to the invention, optionally also in combination with other pharmcologically active substances such as spasmolytics or ⁇ -receptor blockers.
- Suitable forms of use are, for example, tablets, capsules, suppositories, solutions, juices, emulsions or dispersible powders.
- Corresponding tablets can be obtained, for example, by mixing the active ingredient (s) with known auxiliaries, for example inert diluents, such as calcium carbonate, calcium phosphate or lactose, disintegrants, such as corn starch or alginic acid, binders, such as starch or gelatin, lubricants, such as magnesium stearate or talc, and / or agents to achieve the depot effect, such as carboxypolymethylene, carboxymethyl cellulose, cellulose acetate phthalate, or polyvinyl acetate.
- auxiliaries for example inert diluents, such as calcium carbonate, calcium phosphate or lactose, disintegrants, such as corn starch or alginic acid, binders, such as starch or gelatin, lubricants, such as magnesium stearate or talc, and / or agents to achieve the depot effect, such as carboxypolymethylene, carboxymethyl cellulose, cellulose acetate phthalate
- coated tablets can be produced by coating cores produced analogously to the tablets with agents conventionally used in coated tablet coatings, for example collidone or shellac, gum arabic, talc, titanium dioxide or sugar.
- the core can also consist of several layers to achieve a deposit effect or to avoid incompatibilities.
- the coated tablet shell can also consist of several layers in order to achieve a depot effect, it being possible to use the auxiliaries mentioned above for the tablets.
- Juices of the active substances or combinations of active substances according to the invention can additionally contain a sweetener such as saccharin, cyclamate, glycerol or sugar as well as a taste-improving agent, e.g. Flavorings, such as vanillin or orange extract, contain. You can also use suspension aids. or thickeners, such as sodium carboxymethyl cellulose, wetting agents, for example condensation products of fatty alcohols with ethylene oxide, or protective substances, such as p-hydroxybenzoates.
- a sweetener such as saccharin, cyclamate, glycerol or sugar
- a taste-improving agent e.g. Flavorings, such as vanillin or orange extract
- You can also use suspension aids. or thickeners, such as sodium carboxymethyl cellulose, wetting agents, for example condensation products of fatty alcohols with ethylene oxide, or protective substances, such as p-hydroxybenzoates.
- Injection solutions are made in the usual way, e.g. with the addition of preservatives, such as p-hydroxybenzoates, or stabilizers, such as alkali metal salts of ethylenediaminetetraacetic acid, and filled into injection bottles or ampoules.
- preservatives such as p-hydroxybenzoates, or stabilizers, such as alkali metal salts of ethylenediaminetetraacetic acid, and filled into injection bottles or ampoules.
- the capsules containing one or more active ingredients or combinations of active ingredients can be produced, for example, by mixing the active ingredients with inert carriers, such as milk sugar or sorbitol, and encapsulating them in gelatin capsules.
- inert carriers such as milk sugar or sorbitol
- Suitable suppositories can be produced, for example, by mixing them with carriers, such as neutral fats or polyethylene glycol or its derivatives.
- 1 coated tablet contains:
- the mixture of the active substance with milk sugar and corn starch is granulated with a 10% aqueous gelatin solution through a sieve with a mesh size of 1 mm, dried at 40 ° C. and passed through a sieve again.
- the granules obtained in this way are mixed with magnesium stearate and pressed.
- the cores obtained in this way are coated in a conventional manner with a casing which is applied with the aid of an aqueous suspension of sugar, titanium dioxide, talc and gum arabic.
- the finished coated tablets are polished with beeswax. Dragee final weight: 100 mg
- the active ingredient and magnesium stearate are granulated with an aqueous solution of the soluble starch, the granules are dried and mixed intimately with milk sugar and corn starch. The mixture is then compressed into tablets of 100 mg weight, each containing 0.5 mg of active ingredient.
- 1 suppository contains:
- the finely powdered substance is stirred into the molten suppository mass, which has been cooled to 40 ° C., using an immersion homogenizer.
- the mass is poured into slightly pre-cooled molds at 35 ° C.
- the active ingredient and the excipients are dissolved in a sufficient amount of water and brought to the desired concentration with the necessary amount of water.
- the solution is filtered and filled into 1 ml ampoules under aseptic conditions. Finally, the ampoules are sterilized and sealed. Each ampoule contains 0.5 mg of active ingredient.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Claims (5)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2732943 | 1977-07-21 | ||
DE19772732921 DE2732921A1 (de) | 1977-07-21 | 1977-07-21 | Neue substituierte 1-acyl-piperidino- bzw. -piperazino-4h-s-triazolo eckige klammer auf 3,4c eckige klammer zu thieno eckige klammer auf 2,3e eckige klammer zu 1,4- diazepine, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen |
DE19772732943 DE2732943A1 (de) | 1977-07-21 | 1977-07-21 | Neue substituierte 1-piperazinyl- 4h-s-triazolo eckige klammer auf 3,4c eckige klammer zu thieno eckige klammer auf 2,3e eckige klammer zu 1,4-diazepine, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen |
DE2732921 | 1977-07-21 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0000479A1 EP0000479A1 (fr) | 1979-02-07 |
EP0000479B1 true EP0000479B1 (fr) | 1981-01-07 |
Family
ID=25772369
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP78100263A Expired EP0000479B1 (fr) | 1977-07-21 | 1978-06-28 | 1-Pipérazinyl-4H-s-triazolo (3,4-c)thiéno (2,3-e)1,4-diazépines, procédé pour leur préparation et médicaments les contenant |
Country Status (30)
Country | Link |
---|---|
US (1) | US4180573A (fr) |
EP (1) | EP0000479B1 (fr) |
JP (1) | JPS5422395A (fr) |
AT (1) | AT363949B (fr) |
AU (1) | AU515885B2 (fr) |
CA (1) | CA1087182A (fr) |
CH (1) | CH642374A5 (fr) |
CS (1) | CS209897B2 (fr) |
DD (1) | DD137934A5 (fr) |
DE (1) | DE2860404D1 (fr) |
DK (1) | DK150306C (fr) |
ES (2) | ES471886A1 (fr) |
FI (1) | FI63033C (fr) |
FR (1) | FR2398070A1 (fr) |
GB (1) | GB2001972B (fr) |
GR (1) | GR65022B (fr) |
HU (1) | HU176485B (fr) |
IE (1) | IE47336B1 (fr) |
IL (1) | IL55169A (fr) |
IT (1) | IT1107490B (fr) |
LU (1) | LU80002A1 (fr) |
NL (1) | NL7807762A (fr) |
NO (1) | NO149889C (fr) |
NZ (1) | NZ187915A (fr) |
PH (1) | PH14236A (fr) |
PL (1) | PL115061B1 (fr) |
PT (1) | PT68330A (fr) |
RO (1) | RO75609A (fr) |
SE (1) | SE439920B (fr) |
SU (2) | SU725564A3 (fr) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2830782A1 (de) * | 1978-07-13 | 1980-01-24 | Boehringer Sohn Ingelheim | Neue substituierte 4h-s-triazolo eckige klammer auf 3,4c eckige klammer zu thieno eckige klammer auf 2,3e eckige klammer zu 1,4-diazepine, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen |
ES2037013T3 (es) * | 1986-01-21 | 1993-06-16 | Boehringer Ingelheim Kg | Procedimiento para preparar tieno-1,4-diazepinas. |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
PH12303A (en) * | 1973-02-08 | 1979-01-16 | Hoffmann La Roche | Thienotriazolodiazepine derivatives |
AT338799B (de) * | 1974-03-02 | 1977-09-12 | Boehringer Sohn Ingelheim | Verfahren zur herstellung neuer substituierter 6-aryl-4h-s-triazolo-(3,4c)-thieno-(2,3e)-1,4-diazepine und ihrer salze |
US3894025A (en) * | 1974-03-21 | 1975-07-08 | Upjohn Co | 1-Piperazino-6-phenyl-4H-s-triazolo{8 4,3-a{9 {8 1,4{9 -benzodiazepine compounds |
JPS5747916B2 (fr) * | 1974-05-13 | 1982-10-13 | ||
DE2503235A1 (de) * | 1975-01-27 | 1976-07-29 | Boehringer Sohn Ingelheim | Neues verfahren zur herstellung von 8-brom-thieno-triazolo-1,4-diazepinen |
DE2531678C3 (de) * | 1975-07-16 | 1979-06-28 | C.H. Boehringer Sohn, 6507 Ingelheim | Thieno [2,3e] triazole [3,4c] 5,6-dihydro-l,4diazepine und Verfahren zu ihrer Herstellung |
DE2533924C3 (de) * | 1975-07-30 | 1979-05-03 | C.H. Boehringer Sohn, 6507 Ingelheim | Verfahren zur Herstellung von 6- Aryl-4H-striazolo [3,4-c] thieno [2,3-e] 1,4-diazepinen |
-
1978
- 1978-06-26 FI FI782025A patent/FI63033C/fi not_active IP Right Cessation
- 1978-06-28 EP EP78100263A patent/EP0000479B1/fr not_active Expired
- 1978-06-28 DE DE7878100263T patent/DE2860404D1/de not_active Expired
- 1978-07-07 GR GR56728A patent/GR65022B/el unknown
- 1978-07-11 AT AT0498978A patent/AT363949B/de not_active IP Right Cessation
- 1978-07-13 US US05/924,149 patent/US4180573A/en not_active Expired - Lifetime
- 1978-07-17 PH PH21384A patent/PH14236A/en unknown
- 1978-07-18 RO RO7894710A patent/RO75609A/fr unknown
- 1978-07-18 CH CH772878A patent/CH642374A5/de not_active IP Right Cessation
- 1978-07-19 LU LU80002A patent/LU80002A1/de unknown
- 1978-07-19 IL IL55169A patent/IL55169A/xx unknown
- 1978-07-19 CS CS784821A patent/CS209897B2/cs unknown
- 1978-07-19 SU SU782638749A patent/SU725564A3/ru active
- 1978-07-19 IT IT50381/78A patent/IT1107490B/it active
- 1978-07-20 GB GB7830584A patent/GB2001972B/en not_active Expired
- 1978-07-20 DK DK325178A patent/DK150306C/da not_active IP Right Cessation
- 1978-07-20 IE IE1456/78A patent/IE47336B1/en unknown
- 1978-07-20 SE SE7808019A patent/SE439920B/sv not_active IP Right Cessation
- 1978-07-20 HU HU78BO1726A patent/HU176485B/hu unknown
- 1978-07-20 PL PL1978208542A patent/PL115061B1/pl unknown
- 1978-07-20 NL NL7807762A patent/NL7807762A/xx not_active Application Discontinuation
- 1978-07-20 PT PT68330A patent/PT68330A/pt unknown
- 1978-07-20 AU AU38209/78A patent/AU515885B2/en not_active Expired
- 1978-07-20 ES ES471886A patent/ES471886A1/es not_active Expired
- 1978-07-20 NZ NZ187915A patent/NZ187915A/xx unknown
- 1978-07-20 DD DD78206830A patent/DD137934A5/xx unknown
- 1978-07-20 NO NO782499A patent/NO149889C/no unknown
- 1978-07-20 JP JP8889078A patent/JPS5422395A/ja active Granted
- 1978-07-20 CA CA307,798A patent/CA1087182A/fr not_active Expired
- 1978-07-21 FR FR7821744A patent/FR2398070A1/fr active Granted
- 1978-08-24 ES ES472812A patent/ES472812A1/es not_active Expired
-
1979
- 1979-04-04 SU SU792746903A patent/SU793402A3/ru active
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE19636769A1 (de) | 3-Substituierte Pyrido [4',3':4,5]thieno[2,3-d]pyrimidin-Derivate, ihre Herstellung und Verwendung | |
EP0163260B1 (fr) | Nouvelles pyrrolidones substituées, procédé pour leur préparation et médicaments | |
EP0044989B1 (fr) | 5,10-Dihydro-11H-dibenzo(b,e)(1,4)diazépin-11-ones substituées en position 5, procédé pour leur préparation et médicaments les contenant | |
EP0132811B1 (fr) | Hydroxyméthyl-4 pyrrolidinones substituées en position 1, procédés pour leur préparation, compositions pharmaceutiques et produits intermédiaires | |
EP0288048B1 (fr) | Dérivés de benzo- et thiéno-3,4-dihydropyridine, procédés pour leur préparation et médicaments les contenant | |
EP0180115A2 (fr) | 1,2,4-Triazolyl carbamates et leurs sels d'addition acides, procédé pour leur préparation et médicaments | |
DE10004572A1 (de) | Neue positive allosterische AMPA-Rezeptor Modulatoren (PAARM), Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel | |
EP0000479B1 (fr) | 1-Pipérazinyl-4H-s-triazolo (3,4-c)thiéno (2,3-e)1,4-diazépines, procédé pour leur préparation et médicaments les contenant | |
DE2749584A1 (de) | Ueberbrueckte geminale diphenylpiperidine, verfahren zu ihrer herstellung und sie enthaltende arzneimittel | |
DE1795176A1 (de) | Neue,in 5-Stellung substitutierte 5,10-Dihydro-11H-dibenzo-[b,e][1,4]diazepin-11-one und Verfahren zu ihrer Herstellung | |
DE4019080A1 (de) | Neue 3,7-diazabicycolo (3,3,1)nonan-verbindungen enthaltende arzneimittel | |
EP0280290B1 (fr) | Remède à activité antidépressive | |
EP0137993B1 (fr) | 11-Pipérazinyl-5H-imidazo[2,1-c][1,4]benzodiazépines, procédé pour leur préparation et intermédiaires et médicaments les contenant | |
DE2732921A1 (de) | Neue substituierte 1-acyl-piperidino- bzw. -piperazino-4h-s-triazolo eckige klammer auf 3,4c eckige klammer zu thieno eckige klammer auf 2,3e eckige klammer zu 1,4- diazepine, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen | |
EP0132541A2 (fr) | Dérivés de 2-propanol, leur procédé de préparation, et les médicaments les contenant | |
CH639976A5 (de) | 2,6-bis-(aminoacylamino)-benzo-(1,2-d:5,4-d')-bisthiazole und 2-amino-6-(aminoacylamino)-benzo-(1,2-d:5,4-d')-bisthiazole und diese verbindungen enthaltende arzneimittel. | |
DE2460776C2 (de) | 1-substituierte 6-Aryl-4H-s-triazolo-(3,4c)-thieno-(2,3e)-1,4-diazepine, Verfahren zu ihrer Herstellung, diese enthaltende pharmazeutische Präparate sowie Zwischenprodukte und Verfahren zur Herstellung dieser Zwischenprodukte | |
EP0024582A1 (fr) | Benzodiazépinones, procédé pour leur préparation et médicaments les contenant | |
DE2345422A1 (de) | Neue substituierte arylpiperazine, deren saeureadditionssalze, diese enthaltende arzneimittel sowie verfahren zu deren herstellung | |
DE2830782A1 (de) | Neue substituierte 4h-s-triazolo eckige klammer auf 3,4c eckige klammer zu thieno eckige klammer auf 2,3e eckige klammer zu 1,4-diazepine, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen | |
DE3718570A1 (de) | Benzo- und thieno-3,4-dihydro-1- pyridinylessigsaeurederivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel | |
AT376980B (de) | Verfahren zur herstellung neuer pyrido(1,2-a)pyrimidin-derivate, von deren pharmazeutisch akzeptablen salzen sowie deren solvaten, stereoisomeren und tautomeren | |
DE2435041B2 (de) | 8-substituierte 6-aryl-4h-s-triazolo eckige klammer auf 3,4c eckige klammer zu thieno eckige klammer auf 2,3e eckige klammer zu 1,4-diazepine, verfahren zu ihrer herstellung, ihre verwendung in arzneimitteln und diese enthaltende pharmazeutische praeparate | |
EP0014996A1 (fr) | Spiro-amidines hétérocycliques, leurs stéréoisomères et isomères optiques, procédés pour leur préparation et médicaments les contenant | |
DE3717069A1 (de) | 5-substituierte 10-cyanmethylen-thieno(3,4-b)-benzo-azepine |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
AK | Designated contracting states |
Designated state(s): DE NL |
|
17P | Request for examination filed | ||
GRAA | (expected) grant |
Free format text: ORIGINAL CODE: 0009210 |
|
AK | Designated contracting states |
Designated state(s): DE NL |
|
REF | Corresponds to: |
Ref document number: 2860404 Country of ref document: DE Date of ref document: 19810226 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: DE Payment date: 19840620 Year of fee payment: 7 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: NL Payment date: 19870630 Year of fee payment: 10 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: NL Effective date: 19900101 |
|
NLV4 | Nl: lapsed or anulled due to non-payment of the annual fee | ||
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: DE Effective date: 19900301 |
|
PLBE | No opposition filed within time limit |
Free format text: ORIGINAL CODE: 0009261 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT |