EP0000299B1 - Neue substituierte 2-Benzoyl-4-chloro-glycinanilidederivate, Verfahren zu ihrer Herstellung und deren Verwendung als Heilmittel. - Google Patents
Neue substituierte 2-Benzoyl-4-chloro-glycinanilidederivate, Verfahren zu ihrer Herstellung und deren Verwendung als Heilmittel. Download PDFInfo
- Publication number
- EP0000299B1 EP0000299B1 EP78400009A EP78400009A EP0000299B1 EP 0000299 B1 EP0000299 B1 EP 0000299B1 EP 78400009 A EP78400009 A EP 78400009A EP 78400009 A EP78400009 A EP 78400009A EP 0000299 B1 EP0000299 B1 EP 0000299B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- chloro
- benzoyl
- general formula
- methyl
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 0 CC(CC(*)C=C1)=C1N(*)*=O Chemical compound CC(CC(*)C=C1)=C1N(*)*=O 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N OCc1ccccc1 Chemical compound OCc1ccccc1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/15—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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
-
- 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
Definitions
- the present invention carried out at the PIERRE FABRE Research Center relates to new derivatives of substituted 2-benzoyl-4-chloro-glycinanilides, their preparation process and their application as medicaments.
- the present invention however relates to derivatives which differ from those of the aforementioned prior art by a substitution on the first nitrogen atom in the glycynanilide series, corresponding to the formula:
- Alkyl groups denote straight or branched chain alkyl groups, such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec.butyl, tert.-butyl, pentyl, isopentyl, neopentyl, tert.pentyl, hexyl, isohexyl, heptyle, etc.
- the alkoxy substituents can for example be chosen from methoxy, ethoxy, propoxy, isopropoxy, etc. groups.
- the aralkyl groups can be chosen from benzyl, phenethyl, phenylpropyl, etc.
- the alkenyl groups can be chosen from allyl, butenyl, pentadienyl groups, etc.
- the alkynyl groups can be chosen from ethynyl, propargyl, etc.
- saturated or unsaturated heterocycles are chosen for example from pyrrolyl, imidazolyl, pyrazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrinidinyl, pyridazinyl, pyrrolidinyl, imidazolidinyl, pyrazolidinyl, piperidyl, piperazinyl, morpholinyl, etc.
- the present invention also applies to the salts of the compounds of formula 1 obtained with therapeutically acceptable acids.
- therapeutically or physiologically acceptable addition salts mention may be made of the salts of mineral acids, such as hydrochloric, phosphoric and sulfuric acids, and the salts of organic acids, such as succinic acids. , tartaric, etc.
- the present invention finally relates to the application of the compounds of general formula I as medicaments with activity on the central nervous system and in particular as anxiolytic, sedative, anticonvulsant, hypnotic agents or as muscle relaxant.
- the crystals are recovered by filtration, then these crystals are dissolved in two liters of ethyl acetate, the aqueous phase formed is decanted, the organic phase is dried over sodium sulfate and discolored by addition of animal black. After filtration, the organic phase is evaporated. A crude crystallized residue is recovered which is triturated in petroleum ether. The coloration partly disappears and 330 g of pale yellow crystals are obtained after filtration and drying. Yield 95%.
- the mixture is stirred at ambient temperature for 6 hours and left to stand overnight, then the mixture is brought to 50 ° C. for 2 hours and to 70 ° C. for 3 hours.
- the free base is poured into 6 liters of ice water, released and crystallized.
- the crystals are recovered by filtration. These crystals are dissolved in 1.5 liters of ethyl acetate, the aqueous phase is decanted and the organic phase is dried over sodium sulfate. After filtration and concentration, 124.5 g of yellow crystals are recovered. 85% yield.
- 2-methyl-5-chloro-benzophenone can also be prepared by direct methylation of 2-amino-5-chloro-benzophenone according to the following procedure:
- the organic phase is dried over sodium sulfate.
- the mixture After addition of the brominated derivative, the mixture is heated for 6 hours at 45 ° C., then left to stand overnight and evaporated to dryness under reduced pressure. The residue is taken up in a bicarbonate solution and extracted with ethyl acetate. Washed with water, dried over sodium sulfate and discolored in animal black. After filtration, evaporated to dryness. The residual oil is treated with an ethanolic solution saturated with hydrochloric acid.
- Solubility soluble in water at 1%.
- Solubility soluble in water at 1%.
- the compounds of the present invention endowed with remarkable activity on the central nervous system, are therefore capable of being administered to humans or to animals: orally or by injection, in the form of a base. free or one of its therapeutically acceptable salts.
- the compounds of the present invention have been subjected to toxicity controls.
- the toxicity of certain compounds determined by the lethal dose 50 is reported in the following table. It was tested on batches of 10 mice by oral, intraperitoneal and intravenous route in certain cases, and calculated according to the method of MILLER and TAINTER (Proc. Soc. Exper. Biol. Méd., 1944, 57,261) .
- mice have tonic convulsions whose outcome is fatal.
- the compound is administered orally 60 minutes before the injection of pentamethylenetetrazole.
- the animals are observed for 2 hours after administration of pentamethylenetetrazole. In certain specific cases the tests have been confirmed intraperitoneally.
- the results are expressed by the effective dose of DE 50 (Goodman and Col. ⁇ J. Pharmacol. 108, 1953).
- mice This test is carried out on male Swiss strain mice.
- the mouse is placed on a wooden rod with a diameter of 3 cm, rotating at the rate of 5 revolutions / minute. Mice are chosen which can remain on the rod for at least 3 minutes during successive tests and they are grouped together in groups of 10 for the test of each dose. If the mouse falls from the stem in less than 2 minutes, the compound tested is considered to be effective.
- the results are expressed by the effective dose DE 50 according to NW DUNHAN and TS MIVA-J. bitter. pharm. Ass., 1957, 46, 208.
- the compounds of the invention and more particularly the compounds of Examples 2, 10, 11, 14, 19 and 20 can be used therapeutically in the treatment of anxiety and neuroses.
- These compounds and their therapeutically compatible acid addition salts can be used as medicaments, for example in the form of pharmaceutical preparations suitable for enteral or parenteral administration, with for example water, lactose, gelatin, starches , magnesium stearate, talc, vegetable oils, gums, polyalkylene glycols, petroleum jelly, etc.
- preparations can be in solid form, for example tablets, dragees, capsules, etc. or in liquid form, for example solutions, suspensions or emulsions.
- compositions in a form suitable for injection are preferred. These preparations can be subjected to conventional pharmaceutical operations such as sterilization and / or can contain adjuvants, for example preservatives, wetting or emulsification stabilizers, buffer compounds, etc.
- the dosages, to which the active compounds and their therapeutically compatible acid addition salts can be administered can vary in large proportions depending on the condition of the patient.
- a daily dosage of about 0.01 mg to 1 mg per kg of body weight is preferred, however.
- compositions according to the invention can be used in internal medicine, for example in the treatment of organic pathological conditions, such as high blood pressure and coronary artery, accompanied and aggravated by an anxious state; in psychosomatic medicine, for example for the treatment of asthma, peptic ulcers, colopathies and other functional digestive disorders; as well as in psychiatry, for example for the treatment of anxious states of agitation in psychotic subjects.
- organic pathological conditions such as high blood pressure and coronary artery
- psychosomatic medicine for example for the treatment of asthma, peptic ulcers, colopathies and other functional digestive disorders
- psychiatry for example for the treatment of anxious states of agitation in psychotic subjects.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Furan Compounds (AREA)
Claims (27)
mit einem Amin der Formel III
wobei R und X die in Anspruch 20 angegebenen Bedeutungen haben.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR7718511 | 1977-06-16 | ||
FR7718511A FR2403330A1 (fr) | 1977-06-16 | 1977-06-16 | Nouveaux derives de benzoyl-2-chloro-4-glycinanilides substitues, leur procede de preparation et leur application en tant que medicaments |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0000299A1 EP0000299A1 (de) | 1979-01-10 |
EP0000299B1 true EP0000299B1 (de) | 1980-11-12 |
Family
ID=9192181
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP78400009A Expired EP0000299B1 (de) | 1977-06-16 | 1978-06-01 | Neue substituierte 2-Benzoyl-4-chloro-glycinanilidederivate, Verfahren zu ihrer Herstellung und deren Verwendung als Heilmittel. |
Country Status (9)
Country | Link |
---|---|
US (1) | US4372975A (de) |
EP (1) | EP0000299B1 (de) |
JP (1) | JPS5436238A (de) |
CA (1) | CA1124256A (de) |
DE (1) | DE2860270D1 (de) |
ES (1) | ES470861A1 (de) |
FR (1) | FR2403330A1 (de) |
IT (1) | IT1156820B (de) |
ZA (1) | ZA783410B (de) |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2436776A1 (fr) * | 1978-09-25 | 1980-04-18 | Fabre Sa Pierre | Nouveaux derives d'ortho chloro benzoyl-2 chloro-4 glycylanilide, leur preparation et leur application en tant que medicaments |
FR2449677B1 (fr) * | 1979-02-26 | 1986-03-28 | Fabre Sa Pierre | Nouveaux derives de benzoyl-2 glycylanilides substitues, leur preparation et leur application en tant que medicaments anxiolytiques |
FR2459793A1 (fr) * | 1979-06-25 | 1981-01-16 | Fabre Sa Pierre | Nouveaux derives de benzoyl-2 nitro-4 anilides, leur preparation et leur application en tant que medicaments |
FR2492818B1 (fr) * | 1980-10-28 | 1988-03-04 | Fabre Sa Pierre | Ortho halogeno benzoyl-2 halogeno-4 glycylanilides substitues, leur preparation et leur application comme medicaments |
FR2552083B1 (fr) * | 1983-09-15 | 1986-05-09 | Cerm Cent Europ Rech Mauvernay | Derives de (alkynyloxy-3 hydroxy-2-propyl)-4 piperazinyl-1 n-phenyl acetamide, leur preparation et leur application en therapeutique |
DE4312778C3 (de) * | 1993-04-20 | 2001-10-25 | Vossloh Schwabe Gmbh | Elektrische Anschlußklemmeinrichtung |
US6900228B1 (en) | 1998-03-10 | 2005-05-31 | Research Triangle Institute | Opiate compounds, methods of making and methods of use |
AU2003248549B2 (en) * | 2002-05-24 | 2010-04-08 | Millennium Pharmaceuticals, Inc. | CCR9 inhibitors and methods of use thereof |
US7741519B2 (en) | 2007-04-23 | 2010-06-22 | Chemocentryx, Inc. | Bis-aryl sulfonamides |
US7227035B2 (en) * | 2002-11-18 | 2007-06-05 | Chemocentryx | Bis-aryl sulfonamides |
US7420055B2 (en) | 2002-11-18 | 2008-09-02 | Chemocentryx, Inc. | Aryl sulfonamides |
US20070021466A1 (en) * | 2002-11-18 | 2007-01-25 | Solomon Ungashe | CCR2 inhibitors and methods of use thereof |
JP4611746B2 (ja) * | 2002-11-18 | 2011-01-12 | ケモセントリックス, インコーポレイテッド | アリールスルホンアミド |
US20060111351A1 (en) * | 2002-11-18 | 2006-05-25 | Solomon Ungashe | Aryl sulfonamides |
CN105001105A (zh) * | 2015-06-26 | 2015-10-28 | 华中药业股份有限公司 | 一种2-甲氨基-5-氯二苯甲酮的制备方法 |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DK104746C (da) * | 1960-06-27 | 1966-06-27 | Hoffmann La Roche | Fremgangsmåde til fremstilling af 2-α-aminoalkanoylamido-benzophenon-forbindelser eller syreadditionssalte eller kvaternære ammoniumforbindelser deraf. |
US3202699A (en) * | 1961-07-11 | 1965-08-24 | Hoffmann La Roche | Carbobenzoxyglycylamino-benzophenones |
US3914215A (en) * | 1967-11-27 | 1975-10-21 | Sankyo Co | Benzodiazepine derivatives and process for preparing the same |
BG17604A3 (de) * | 1968-07-01 | 1973-11-10 | Sankyo Co | |
CA1041498A (en) * | 1968-10-18 | 1978-10-31 | Hoffmann-La Roche Limited | Benzodiazepine derivatives |
US3927010A (en) * | 1969-10-17 | 1975-12-16 | Hoffmann La Roche | Diarylmethane derivatives and processes for their preparation |
SE410732B (sv) * | 1971-12-13 | 1979-10-29 | Sumitomo Chemical Co | Analogiforfarande for framstellning av anilidderivat med terapeutisk verkan |
US3928415A (en) * | 1973-05-08 | 1975-12-23 | Cassella Farbwerke Mainkur Ag | Benzophenone derivatives and process for their production II |
AU471999B2 (en) | 1973-08-10 | 1976-05-13 | Sankyo Company Limited | Substituted amino-acetylamino-benzophenone compounds |
DE2356239A1 (de) * | 1973-11-10 | 1975-05-15 | Cassella Farbwerke Mainkur Ag | Benzophenon-derivate und verfahren zu ihrer herstellung |
JPS5139654A (ja) * | 1974-09-27 | 1976-04-02 | Sumitomo Chemical Co | Aminoasetoaniridojudotai no shinkinaseizoho |
-
1977
- 1977-06-16 FR FR7718511A patent/FR2403330A1/fr active Granted
-
1978
- 1978-06-01 EP EP78400009A patent/EP0000299B1/de not_active Expired
- 1978-06-01 DE DE7878400009T patent/DE2860270D1/de not_active Expired
- 1978-06-14 IT IT49859/78A patent/IT1156820B/it active
- 1978-06-14 ZA ZA00783410A patent/ZA783410B/xx unknown
- 1978-06-15 CA CA305,549A patent/CA1124256A/fr not_active Expired
- 1978-06-16 JP JP7314178A patent/JPS5436238A/ja active Pending
- 1978-06-16 ES ES470861A patent/ES470861A1/es not_active Expired
-
1980
- 1980-10-27 US US06/200,622 patent/US4372975A/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
CA1124256A (fr) | 1982-05-25 |
ZA783410B (en) | 1979-06-27 |
IT7849859A0 (it) | 1978-06-14 |
DE2860270D1 (en) | 1981-02-05 |
FR2403330B1 (de) | 1982-11-05 |
FR2403330A1 (fr) | 1979-04-13 |
US4372975A (en) | 1983-02-08 |
ES470861A1 (es) | 1979-02-01 |
IT1156820B (it) | 1987-02-04 |
JPS5436238A (en) | 1979-03-16 |
EP0000299A1 (de) | 1979-01-10 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CA1202639A (fr) | Derives d'aryl-1 aminomethyl-2 cyclopropanes carboxamides (z) et leur preparation | |
EP0000299B1 (de) | Neue substituierte 2-Benzoyl-4-chloro-glycinanilidederivate, Verfahren zu ihrer Herstellung und deren Verwendung als Heilmittel. | |
EP0487408A1 (de) | Oxazolopyridinderivate, Verfahren zu ihrer Herstellung und die sie enthaltenden pharmazeutischen Zusammensetzungen | |
FR2468601A1 (fr) | Nouveaux derives de flavanne utiles notamment comme anticonvulsivants | |
EP0068998B1 (de) | (Z)-1-Aryl-2-aminomethyl-cyclopropan-carboxylate, ihre Herstellung und ihre Verwendung als Arzneimittel für die Behandlung von verschiedenen Schmerzen | |
EP0205362A1 (de) | Chinolylglycinamidderivate, Verfahren zu ihrer Herstellung und therapeutische Verwendung als Psychotrope | |
EP0239461A1 (de) | N-¬¬(Hydroxy-2-phenyl)(phenyl)methylen amino-2 äthylacetamid-Derivate, Verfahren zu ihrer Herstellung und ihre Anwendung als Heilmittel | |
EP0076199B1 (de) | Triazoloquinazolone und deren Salze, Verfahren und Zwischenprodukte zu ihrer Herstellung, ihre Verwendung als Arzneimittel und diese enthaltende Zusammensetzungen | |
EP0015214B1 (de) | Substituierte 2-(Benzoyl)-glycinanilid-Derivate, ihre Herstellung und ihre Verwendung in anxiolytischen Arzneimitteln | |
EP0002978B1 (de) | Thiazolidindion-2,4 Derivate, deren Herstellung und Verwendung als Arzneimittel | |
EP0114770A2 (de) | Verbindungen mit diazotiertem heterocyclischem Kern, Verfahren zu deren Herstellung und diese enthaltende, auf das zentrale Nervensystem wirkende Arzneimittel | |
EP0301936B1 (de) | Piperidin-Derivate, deren Herstellung und deren Verwendung als Heilmittel | |
EP0077720B1 (de) | Derivate von Biphenyl-Alkyl-Carboxylaten, deren Herstellungsverfahren und deren Verwendung als Arzneimittel | |
FR2643634A1 (fr) | Nouveaux derives benzoxazolinoniques, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent | |
EP0022017B1 (de) | Derivate von 2-Benzoyl-4-nitro-aniliden, deren Herstellung und deren Verwendung als Heilmittel | |
FR2645743A1 (fr) | Compositions therapeutiques a base de derives di-substitues des n,n(prime)-ditrimethoxybenzoyle piperazines | |
EP0087337B1 (de) | 2-Piperazinyl-4-phenyl-quinazolin-Derivate mit antidepressiven Eigenschaften, Verfahren zu deren Herstellung und diese enthaltende Arzneimitteln | |
EP0010030B1 (de) | 2'-(Ortho-chlor-benzoyl),4'-chlor-glycinanilid-Derivate, ihre Herstellung und ihre Verwendung als Arzneimittel | |
CA2045849A1 (fr) | Derives d'oxazolo pyridines, leur procede de preparation et les compositions pharmaceutiques qui les contiennent | |
EP0161143B1 (de) | 1,2,4-Thiadiazine und ihre Salze, Verfahren und Zwischenprodukte zu ihrer Herstellung, ihre Verwendung als Arzneimittel und sie enthaltende Arzneimittel | |
EP0035619B1 (de) | 3-Amino-(1H,3H)-2,4-chinazolindionderivate | |
EP0067094A1 (de) | Heterocyclische Derivate von Amidoxinen, ihre Herstellung und therapeutische Verwendung | |
CA1207768A (fr) | Carboxamidoguanidines, leur procede d'obtention et les compositions pharmaceutiques en renfermant | |
CH618171A5 (en) | Process for the preparation of new imidazolobenzodiazepines and of their salts | |
FR2539414A1 (fr) | Derives de la pyrimidine, leur procede de preparation et les medicaments ayant une activite sur le systeme nerveux central qui en contiennent |
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): BE CH DE FR GB NL |
|
17P | Request for examination filed | ||
GRAA | (expected) grant |
Free format text: ORIGINAL CODE: 0009210 |
|
AK | Designated contracting states |
Designated state(s): BE CH DE FR GB NL |
|
REF | Corresponds to: |
Ref document number: 2860270 Country of ref document: DE Date of ref document: 19810205 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: GB Payment date: 19910524 Year of fee payment: 14 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: CH Payment date: 19910610 Year of fee payment: 14 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: DE Payment date: 19910620 Year of fee payment: 14 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: FR Payment date: 19910626 Year of fee payment: 14 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: NL Payment date: 19910630 Year of fee payment: 14 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: BE Payment date: 19910715 Year of fee payment: 14 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: GB Effective date: 19920601 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: CH Effective date: 19920630 Ref country code: BE Effective date: 19920630 |
|
BERE | Be: lapsed |
Owner name: PIERRE FABRE S.A. Effective date: 19920630 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: NL Effective date: 19930101 |
|
GBPC | Gb: european patent ceased through non-payment of renewal fee |
Effective date: 19920601 |
|
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: FR Effective date: 19930226 |
|
REG | Reference to a national code |
Ref country code: CH Ref legal event code: PL Ref country code: CH Ref legal event code: AUV Free format text: LE BREVET CI-DESSUS EST TOMBE EN DECHEANCE FAUTE DE PAIEMENT, DE LA 15E ANNUITE. |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: DE Effective date: 19930302 |
|
REG | Reference to a national code |
Ref country code: FR Ref legal event code: ST |
|
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 |