CH657126A5 - BENZAMIDO AND DIAZEPINES COMPOUNDS. - Google Patents
BENZAMIDO AND DIAZEPINES COMPOUNDS. Download PDFInfo
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- CH657126A5 CH657126A5 CH65/85A CH6585A CH657126A5 CH 657126 A5 CH657126 A5 CH 657126A5 CH 65/85 A CH65/85 A CH 65/85A CH 6585 A CH6585 A CH 6585A CH 657126 A5 CH657126 A5 CH 657126A5
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- 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
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- 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
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- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/38—[b, e]- or [b, f]-condensed with six-membered rings
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Description
La présente invention concerne de nouveaux composés du type benzamido et diazépine utiles pour la préparation de nouvelles (ami-noalkyl)-5-phényl-l l-5H-dibenzo-[b,e][l,4]-diazépines ayant des propriétés antidépressantes. The present invention relates to new compounds of the benzamido and diazepine type useful for the preparation of new (ami-noalkyl) -5-phenyl-1 l-5H-dibenzo- [b, e] [1,4] -diazepines having properties antidepressants.
Les nouveaux composés répondent à la formule IIb telle que définie dans la revendication 1. The new compounds correspond to formula IIb as defined in claim 1.
L'invention concerne en plus l'utilisation de ces nouveaux composés telle que définie dans la revendication 2 et les nouveaux composés de formule III ainsi obtenus. The invention further relates to the use of these new compounds as defined in claim 2 and to the new compounds of formula III thus obtained.
Le brevet britannique N° 907 646 décrit la préparation de certaines des dibenzodiazépines utiles comme médicaments selon l'invention; par exemple, l'ingrédient actif du composé de l'exemple 1 ci-après sous forme de maléate. British Patent No. 907,646 describes the preparation of some of the dibenzodiazepines useful as medicaments according to the invention; for example, the active ingredient of the compound of Example 1 below in the form of maleate.
Le brevet britannique N° 959 994 décrit l'utilité de formes réduites, par exemple des (aminoalkyl)-5 phényl-11 dihydro-10,11 5H-dibenzo[b,e][l,4]diazépines comme parasympatholytiques, antihista-miniques, spasmolytiques, tranquillisants et psychostimulants. British Patent No. 959,994 describes the usefulness of reduced forms, for example (aminoalkyl) -5-phenyl-11 dihydro-10.11 5H-dibenzo [b, e] [1,4] diazepines as parasympatholytics, antihistra mineral, spasmolytic, tranquilizers and psychostimulants.
Greig, M.E. et coll., dans «J. Med. Chem.», 14, N° 2, page 153 (1971), décrivent l'activité anaphylactique de certains homologues Greig, M.E. et al., In “J. Med. Chem. ”, 14, No. 2, page 153 (1971), describe the anaphylactic activity of certain homologs
(CH2)3nr1R2 (CH2) 3nr1R2
où R1 et R2 représentent un atome d'hydrogène ou un radical méthyle, et X représente un atome d'hydrogène, de chlore, de brome ou de fluor, et leurs sels d'addition d'acides convenant en pharmacie. where R1 and R2 represent a hydrogen atom or a methyl radical, and X represents a hydrogen, chlorine, bromine or fluorine atom, and their acid addition salts suitable in pharmacy.
Les composés où R1 et R2 représentent tous deux un atome d'hydrogène, ou un représente un radical méthyle et l'autre un atome d'hydrogène, sont nouveaux. The compounds in which R1 and R2 both represent a hydrogen atom, or one represents a methyl radical and the other represents a hydrogen atom, are new.
Les sels d'addition d'acides acceptables en pharmacie sont les sels physiologiquement compatibles, tels que les sels formés avec des acides forts ou faibles. On peut citer comme exemples d'acides forts les acides chlorhydrique, sulfurique et phosphorique. On peut citer comme exemples d'acides faibles les acides fumarique, maléique, succinique, oxalique, cyclohexamique et similaires. The pharmaceutically acceptable acid addition salts are physiologically compatible salts, such as the salts formed with strong or weak acids. Examples of strong acids that may be mentioned include hydrochloric, sulfuric and phosphoric acids. Examples of weak acids that may be mentioned include fumaric, maleic, succinic, oxalic, cyclohexamic acids and the like.
Pour mettre en évidence l'activité antidépressive des composés de formule I, on a utilisé de la façon suivante la technique décrite par Englehardt, E. L. et coll., «J. Med. Chem.» 11(2):325 (1968), que l'on a déjà utilisée pour indiquer l'utilité de composés pour le traitement de la dépression chez l'homme; on a administré 20 mg/kg du composé à étudier à cinq souris femelles adultes (souche ICR-DUB) par voie intrapéritonéale 30 minutes avant l'administration d'une 35 dose provoquant un ptôsis (32 mg/kg, i-p.) de tétrabénazine (sous forme de méthanesulfonate). 30 mintues après, la présence ou l'absence d'une fermeture complète des paupières (ptôsis) a été déterminée sur chaque animal. On peut, pour chaque composé étudié, établir la DE50 (dose efficace médiane) relative à l'inhibition de la 40 dépression induite par la tétrabénazine chez la souris, selon la technique indiquée par Litchfield et coll., «J. Pharmacol. Exp. Therap.» 96:99-113 (1949). La dibenzodiazépine que l'on préfère est la (dimé-thylamino-3 propyl)-5 phényl-11 5H-dibenzo[b,e][l,4]diazépine. To demonstrate the antidepressant activity of the compounds of formula I, the technique described by Englehardt, E. L. et al., "J. Med. Chem. " 11 (2): 325 (1968), which has already been used to indicate the usefulness of compounds for the treatment of depression in humans; 20 mg / kg of the test compound were administered to five adult female mice (strain ICR-DUB) intraperitoneally 30 minutes before administration of a dose causing ptosis (32 mg / kg, ip.) of tetrabenazine (as methanesulfonate). 30 mintues after, the presence or absence of a complete closure of the eyelids (ptosis) was determined on each animal. One can, for each compound studied, establish the ED50 (median effective dose) relating to the inhibition of depression induced by tetrabenazine in mice, according to the technique indicated by Litchfield et al., "J. Pharmacol. Exp. Therap. " 96: 99-113 (1949). The preferred dibenzodiazepine is (3-dimethylamino-propyl) -5 phenyl-11 5H-dibenzo [b, e] [1,4] diazepine.
D'autres caractéristiques et avantages de l'invention ressortiront 45 de la lecture de la description qui suit et des revendications. Other characteristics and advantages of the invention will emerge from reading the description which follows and the claims.
On peut préparer les nouveaux composés de formule I dont la position 5 est substituée par le radical amino-3-propyle par cyclodéshydratation de nouvelles N-(phtalimido-l)-3-propyl-o-benzamidodi-phénylamines (IIb) puis transformation du radical phtalimido en 50 radical amino (NH2) avec l'hydrazine et un acide. L'équation est la We can prepare the new compounds of formula I whose position 5 is substituted by the amino-3-propyl radical by cyclodehydration of new N- (phthalimido-1) -3-propyl-o-benzamidodi-phenylamines (IIb) then transformation of the phthalimido radical in 50 amino radical (NH2) with hydrazine and an acid. The equation is the
3 3
657 126 657,126
(Ib) (Ib)
l 4 J l 4 J
où X a les significations indiquées pour la formule I. Les composés de formule III sont également nouveaux. where X has the meanings indicated for formula I. The compounds of formula III are also new.
On peut préparer les composés selon l'invention de type benza-mido IIb selon une modification du procédé du brevet britanique N° 907 646 précité. On effectue tout d'abord l'alkylation par réduction de l'o-nitro-diphénylamine avec une solution de (phtalimido-1 )-3 chloro-1 propane, puis on réduit le radical nitro avec de l'hydrogène sur du charbon palladié pour obtenir le composé o-amino correspondant. On fait ensuite réagir le radical amino en position ortho avec un halogénure de benzoyle ou un halogénure de benzoyle substitué. L'équation est la suivante: The compounds according to the invention of benza-mido IIb type can be prepared according to a modification of the method of the British patent No. 907,646 cited above. The alkylation is first carried out by reduction of o-nitro-diphenylamine with a solution of (phthalimido-1) -3 chloro-1 propane, then the nitro radical is reduced with hydrogen on palladium on carbon. to obtain the corresponding o-amino compound. The amino radical is then reacted in the ortho position with a benzoyl halide or a substituted benzoyl halide. The equation is as follows:
(VI) (VI)
.N- .NOT-
i i
H H
1) NaH 1) NaH
2) C1-(CH2)3Q 2) C1- (CH2) 3Q
(V) (V)
CCH2). Q CCH2). Q
(IV) (IV)
(CH2)3 (CH2) 3
Pyridine Pyridine
Exemple 1: Example 1:
A. N-[(phtalimido-1 )-3-propyl]-o-aminodiphénylamine A. N - [(phthalimido-1) -3-propyl] -o-aminodiphenylamine
On fait réagir l'o-nitrodiphénylamine avec l'hydrure de sodium et de (phtalimido-l)-3-chlor-l-propane pour obtenir la N-(phtalimi-do-l)-3-propyl-o-nitrodiphénylamine que l'on réduit ensuite par l'hydrogène sur du charbon palladié dans l'éthanol pour obtenir le composé désiré. O-nitrodiphenylamine is reacted with sodium hydride and (phthalimido-1) -3-chlor-1-propane to obtain the N- (phthalimi-do-1) -3-propyl-o-nitrodiphenylamine that then reduced by hydrogen on palladium on carbon in ethanol to obtain the desired compound.
B. N-(phthalimido-1 )-3-propyl-o-benzamidodiphénylamine B. N- (phthalimido-1) -3-propyl-o-benzamidodiphenylamine
A une solution de 0,0575 mol de N-(phtalimido-l)-3-propyl-o-aminodiphénylamine dans 100 ml de pyridine refroidie à environ 5 C sous atmosphère d'azote, on ajoute 17,8 g (0,0063 mol) de chlorure de benzoyle. On utilise une petite quantité de benzène pour entraîner dans le réacteur le reste de chlorure de benzoyle. On agite le mélange pendant une heure et on bouche le récipient, puis on le place au réfrigérateur pendant le week-end. On évapore ensuite le solvant sous pression réduite. On dissout l'huile résiduelle dans 100 ml de chlorure de méthylène et on lave une fois la solution avec 100 ml d'hydroxyde de sodium 3N et trois fois avec 250 ml d'eau. On sèche la couche de chlorure de méthylène sur du sulfate de magnésium et on évapore sous pression réduite. On chasse ensuite la pryridine résiduelle sous vide poussé (0,26 mbar) pendant une nuit. Le produit est une huile résiduelle, sous la forme de la base libre. To a solution of 0.0575 mol of N- (phthalimido-1) -3-propyl-o-aminodiphenylamine in 100 ml of pyridine cooled to about 5 ° C. under a nitrogen atmosphere, 17.8 g (0.0063) is added. mol) of benzoyl chloride. A small amount of benzene is used to carry the rest of the benzoyl chloride into the reactor. The mixture is stirred for one hour and the container is capped, then placed in the refrigerator over the weekend. The solvent is then evaporated off under reduced pressure. The residual oil is dissolved in 100 ml of methylene chloride and the solution is washed once with 100 ml of 3N sodium hydroxide and three times with 250 ml of water. The methylene chloride layer is dried over magnesium sulfate and evaporated under reduced pressure. The residual pryridine is then removed under high vacuum (0.26 mbar) overnight. The product is a residual oil, in the form of the free base.
Oxalate: A une solution chaude de 4,0 g de la base libre dans l'alcool isopropylique, on ajoute 1,35 g (0,0107 mol) d'acide oxalique dihydraté. Oxalate: To a hot solution of 4.0 g of the free base in isopropyl alcohol, 1.35 g (0.0107 mol) of oxalic acid dihydrate is added.
Exemple 2: Example 2:
Lorsque, selon le mode opératoire de l'exemple 1B, on fait réagir la N-(phtalimido-l)-3-propyl-o-aminodiphénylamine avec chacun des chlorures d'acyle suivants en excès: When, according to the procedure of Example 1B, the N- (phthalimido-1) -3-propyl-o-aminodiphenylamine is reacted with each of the following excess acyl chlorides:
chlorure de chloro-2 benzoyle, 2-chloroyl benzoyl chloride,
chlorure de chloro-3 benzoyle, 3-chloroyl benzoyl chloride,
chlorure de fluoro-2 benzoyle, 2-fluoro benzoyl chloride,
chlorure de fluoro-3 benzoyle, 3-fluoro benzoyl chloride,
chlorure de bromo-2 benzoyle, 2-bromo benzoyl chloride,
chlorure de bromo-3 benzoyle, et chlorure de chloro-4 benzoyle, 3-bromo benzoyl chloride, and 4-chloro benzoyl chloride,
on obtient la N-(phtalimido-l)-3 propyl o-(chloro-la N-(phtalimido-l)-3 propyl o-(chloro-la N-(phtalimido-l)-3 propyl o-(fluoro-la N-(phtalimido-l)-3 propyl o-(fluoro-la N-(phtalimido-l)-3 propyl o-(bromo mine, we obtain N- (phthalimido-l) -3 propyl o- (chloro-la N- (phthalimido-l) -3 propyl o- (chloro-la N- (phthalimido-l) -3 propyl o- (fluoro- N- (phthalimido-l) -3 propyl o- (fluoro-la N- (phthalimido-l) -3 propyl o- (bromo mine,
la N-(phtalimido-l)-3 propyl o-(bromo mine, et N- (phthalimido-1) -3 propyl o- (bromo mine, and
3 la N-(phtalimido-l)-3 propyl o-(chloro 3 N- (phthalimido-1) -3 propyl o- (chloro
Les composés obtenus peuvent être formule I comme suit: The compounds obtained can be formula I as follows:
(IIb) (IIb)
2 benzamido)diphénylamine, 2 benzamido) diphenylamine,
3 benzamido)diphénylamine, 3 benzamido) diphenylamine,
2 benzamido)diphénylamine, 2 benzamido) diphenylamine,
3 benzamido)diphénylamine, -2 benzamido)diphênyla- 3 benzamido) diphenylamine, -2 benzamido) diphenyla-
-3 benzamido)diphényla- -3 benzamido) diphenyla-
-4 benzamido)diphénylamine. transformés en composés de -4 benzamido) diphenylamine. transformed into compounds of
<ÇH2>3 <ÇH2> 3
Q = phtalimido-1. Q = phthalimido-1.
On chauffe à 150° C sous atmosphère d'azote pendant 1,5 heure un mélange agité de 0,05 mol d'un des composés sous-mentionnés et 55 32,19 g (0,2 mol) d'oxychlorure de phosphore dans 50 ml de tétrach-loro-l,l,2,2-êthane. On refroidit quelque peu le mélange et on le verse sur environ 1000 ml de glace pilée, puis on dilue avec suffisamment d'eau pour obtenir un volume final de 1000 ml. On extrait deux fois la suspension aqueuse avec du chlorure de méthylène et on 60 rejette la couche de chlorure de méthylène. On alcalinise la couche avec de l'hydroxyde de sodium 3N et on extrait avec trois portions de 250 ml de chlorure de méthylène. On combine ces trois portions de chlorure de méthylène, on sèche sur sulfate de magnésium et on évapore sous pression réduite pour obtenir une huile résiduelle cons-65 tituée du composé désiré sous la forme de la base libre. On dissout l'huile dans l'alcool isopropylique chaud et on fait réagir avec 4,5 g (0,039 mol) d'acide fumarique. On recueille le fumarate par filtra-tion. Heated at 150 ° C under a nitrogen atmosphere for 1.5 hours a stirred mixture of 0.05 mol of one of the compounds below and 55 32.19 g (0.2 mol) of phosphorus oxychloride in 50 ml of tetrach-loro-l, l, 2,2-ethane. The mixture is cooled slightly and poured onto approximately 1000 ml of crushed ice, then diluted with sufficient water to obtain a final volume of 1000 ml. The aqueous suspension is extracted twice with methylene chloride and the layer of methylene chloride is discarded. The layer was basified with 3N sodium hydroxide and extracted with three 250 ml portions of methylene chloride. These three portions of methylene chloride are combined, dried over magnesium sulfate and evaporated under reduced pressure to obtain a residual oil consisting of the desired compound in the form of the free base. The oil is dissolved in hot isopropyl alcohol and reacted with 4.5 g (0.039 mol) of fumaric acid. The fumarate is collected by filtration.
657126 657126
En employant pour cette réaction les composés suivants: N-(phtalimido-l)-3 propyl o-benzamido)diphênylamine, N-(phtalimido-l)-3 propyl o-(chloro-2 benzamido)diphénylamine, N-(phtalimido-l)-3 propyl o-(chloro-3 benzamido)diphénylamine, N-(phtalimido-I)-3 propyl o-(fluoro-2 benzamido)diphénylamine, N-(phtalimido-l)-3 propyl o-(fluoro-3 benzamido)diphénylamine, N-(phtalimido-l)-3 propyl o-(bromo-2 benzamidojdiphénylamine, N-(phtalimido-l)-3 propyl o-(bromo-3 benzamido)diphênylamine, et Using the following compounds for this reaction: N- (phthalimido-1) -3 propyl o-benzamido) diphenylamine, N- (phthalimido-1) -3 propyl o- (2-chloro benzamido) diphenylamine, N- (phthalimido- l) -3 propyl o- (3-chloro benzamido) diphenylamine, N- (phthalimido-I) -3 propyl o- (2-fluoro benzamido) diphenylamine, N- (phthalimido-1) -3 propyl o- (fluoro- 3 benzamido) diphenylamine, N- (phthalimido-1) -3 propyl o- (2-bromo benzamidojdiphenylamine, N- (phthalimido-1) -3 propyl o- (3-bromo benzamido) diphenylamine, and
N-(phtalimido-l)-3 propyl o-(chloro-4 benzamidojdiphénylamine, on obtient: N- (phthalimido-1) -3 propyl o- (4-chloro benzamidojdiphenylamine, we obtain:
la [(phtalimido-l)-3 propyl]-5 phényl-11 5H-dibenzo[b,e][l,4]diazé-pine, [(phthalimido-1) -3 propyl] -5 phenyl-11 5H-dibenzo [b, e] [1,4] diaze-pine,
la [(phtalimido-l)-3 propyl]-5 (chloro-2 phényl)-! I 5H-dibenzo[b,e]-[l,4]diazépine, [(phthalimido-1) -3 propyl] -5 (2-chloro-phenyl) -! I 5H-dibenzo [b, e] - [l, 4] diazepine,
la [(phtalimido-1 )-3 propyI]-5 (chloro-3 phényl)-! 1 5H-dibenzo[b,e]-[l,4]diazépine, [(phthalimido-1) -3 propyI] -5 (3-chloro-phenyl) -! 1 5H-dibenzo [b, e] - [l, 4] diazepine,
la [(phtalimido-1 )-3 propyl]-5 (fluoro-2 phényl)-l 1 5H-dibenzo[b,e]-[],4]diazépine, [(phthalimido-1) -3 propyl] -5 (2-fluoro phenyl) -1 5H-dibenzo [b, e] - [], 4] diazepine,
s la [(phtalimido-1 )-3 propyl]-5 (fluoro-3 phéynl)-l 1 5H-dibenzo[b,e]-[1,4]diazépine, s [(phthalimido-1) -3 propyl] -5 (fluoro-3 pheynl) -1 5H-dibenzo [b, e] - [1,4] diazepine,
la [(phtalimido-1)-3 propyl]-5 (bromo-2 phényl)-11 5H-dibenzo[b,e]-[l,4]diazépine, [(phthalimido-1) -3 propyl] -5 (2-bromo-phenyl) -11 5H-dibenzo [b, e] - [1,4] diazepine,
la [(phtalimido-1)-3 propyl]-5 (bromo-3 phényl)-11 5H-dibenzo[b,e]-îo [l,4]diazépine, et la [(phtalimido-1)-3 propyl-5 (bromo-3 phényl)-11 5H-dibenzo[b,e]-[l,4]diazépine. [(phthalimido-1) -3 propyl] -5 (bromo-3 phenyl) -11 5H-dibenzo [b, e] -îo [1,4] diazepine, and [(phthalimido-1) -3 propyl- 5 (3-bromo phenyl) -11 5H-dibenzo [b, e] - [1,4] diazepine.
Les composés obtenus sont facilement transformés en leurs 15 chlorhydrates. The compounds obtained are easily transformed into their hydrochlorides.
R R
Claims (3)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30507681A | 1981-09-24 | 1981-09-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH657126A5 true CH657126A5 (en) | 1986-08-15 |
Family
ID=23179221
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH65/85A CH657126A5 (en) | 1981-09-24 | 1981-11-27 | BENZAMIDO AND DIAZEPINES COMPOUNDS. |
| CH7633/81A CH651028A5 (en) | 1981-09-24 | 1981-11-27 | (AMINOALKYL) -5 PHENYL-11 5H-DIBENZO (B, E) (1,4) DIAZEPINES USEFUL AS ANTIDEPRESSANT DRUGS. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH7633/81A CH651028A5 (en) | 1981-09-24 | 1981-11-27 | (AMINOALKYL) -5 PHENYL-11 5H-DIBENZO (B, E) (1,4) DIAZEPINES USEFUL AS ANTIDEPRESSANT DRUGS. |
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| JP (1) | JPS5865280A (en) |
| KR (1) | KR880001866B1 (en) |
| AT (1) | AT383121B (en) |
| AU (2) | AU549806B2 (en) |
| BE (1) | BE891535A (en) |
| CA (1) | CA1199325A (en) |
| CH (2) | CH657126A5 (en) |
| DE (1) | DE3149923A1 (en) |
| DK (1) | DK531281A (en) |
| ES (1) | ES8207157A1 (en) |
| FI (1) | FI813975L (en) |
| FR (1) | FR2513249B1 (en) |
| GB (1) | GB2106894B (en) |
| GR (1) | GR75123B (en) |
| HK (1) | HK85785A (en) |
| HU (1) | HU187394B (en) |
| IE (1) | IE51880B1 (en) |
| IL (1) | IL64257A (en) |
| IN (1) | IN155657B (en) |
| IT (1) | IT1146729B (en) |
| LU (1) | LU83798A1 (en) |
| NL (1) | NL8105892A (en) |
| NO (1) | NO813838L (en) |
| NZ (1) | NZ198986A (en) |
| PH (1) | PH16696A (en) |
| PL (1) | PL234420A1 (en) |
| PT (1) | PT74285B (en) |
| SE (1) | SE448453B (en) |
| SG (1) | SG65485G (en) |
| YU (1) | YU43070B (en) |
| ZA (1) | ZA818481B (en) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB907646A (en) * | 1959-01-23 | 1962-10-10 | Wander S A A | Method of production of new derivatives of diazepin |
| AT228215B (en) * | 1959-01-23 | 1963-07-10 | Wander Ag Dr A | Process for the production of new diazepine derivatives |
| NL256053A (en) * | 1959-09-22 | |||
| AT226721B (en) * | 1959-09-22 | 1963-04-10 | Wander Ag Dr A | Process for the preparation of new, 5-substituted diazepines |
-
1981
- 1981-11-06 SE SE8106594A patent/SE448453B/en not_active IP Right Cessation
- 1981-11-10 IL IL64257A patent/IL64257A/en unknown
- 1981-11-12 NO NO813838A patent/NO813838L/en unknown
- 1981-11-13 IN IN1260/CAL/81A patent/IN155657B/en unknown
- 1981-11-16 GB GB08134501A patent/GB2106894B/en not_active Expired
- 1981-11-17 NZ NZ198986A patent/NZ198986A/en unknown
- 1981-11-17 GR GR66552A patent/GR75123B/el unknown
- 1981-11-25 IE IE2770/81A patent/IE51880B1/en unknown
- 1981-11-25 PH PH26538A patent/PH16696A/en unknown
- 1981-11-27 CH CH65/85A patent/CH657126A5/en not_active IP Right Cessation
- 1981-11-27 CH CH7633/81A patent/CH651028A5/en not_active IP Right Cessation
- 1981-11-27 FR FR8122288A patent/FR2513249B1/en not_active Expired
- 1981-11-27 LU LU83798A patent/LU83798A1/en unknown
- 1981-11-30 DK DK531281A patent/DK531281A/en not_active Application Discontinuation
- 1981-12-07 ZA ZA818481A patent/ZA818481B/en unknown
- 1981-12-09 AT AT0526981A patent/AT383121B/en not_active IP Right Cessation
- 1981-12-10 FI FI813975A patent/FI813975L/en not_active Application Discontinuation
- 1981-12-10 IT IT68607/81A patent/IT1146729B/en active
- 1981-12-15 HU HU813778A patent/HU187394B/en not_active IP Right Cessation
- 1981-12-15 ES ES507970A patent/ES8207157A1/en not_active Expired
- 1981-12-15 AU AU78513/81A patent/AU549806B2/en not_active Ceased
- 1981-12-16 DE DE19813149923 patent/DE3149923A1/en not_active Ceased
- 1981-12-18 BE BE0/206880A patent/BE891535A/en not_active IP Right Cessation
- 1981-12-23 PL PL23442081A patent/PL234420A1/en unknown
- 1981-12-29 JP JP56215952A patent/JPS5865280A/en active Granted
- 1981-12-29 NL NL8105892A patent/NL8105892A/en not_active Application Discontinuation
-
1982
- 1982-01-14 CA CA000394124A patent/CA1199325A/en not_active Expired
- 1982-01-15 PT PT74285A patent/PT74285B/en unknown
- 1982-02-02 KR KR8200419A patent/KR880001866B1/en active
- 1982-03-23 YU YU624/82A patent/YU43070B/en unknown
-
1985
- 1985-09-09 SG SG654/85A patent/SG65485G/en unknown
- 1985-10-18 AU AU48905/85A patent/AU576010B2/en not_active Ceased
- 1985-10-31 HK HK857/85A patent/HK85785A/en unknown
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PFA | Name/firm changed |
Owner name: A. H. ROBINS COMPANY, INCORPORATED (A DELAWARE COR |
|
| PUE | Assignment |
Owner name: AHP SUBSIDIARY (9) CORPORATION |
|
| PL | Patent ceased |