LU82958A1 - BENZYLIDENIC DERIVATIVES, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION - Google Patents
BENZYLIDENIC DERIVATIVES, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION Download PDFInfo
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- LU82958A1 LU82958A1 LU82958A LU82958A LU82958A1 LU 82958 A1 LU82958 A1 LU 82958A1 LU 82958 A LU82958 A LU 82958A LU 82958 A LU82958 A LU 82958A LU 82958 A1 LU82958 A1 LU 82958A1
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- 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
- C07D295/16—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 acylated on ring nitrogen atoms
- C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
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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
- A61P25/08—Antiepileptics; Anticonvulsants
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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
- A61P25/20—Hypnotics; Sedatives
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Description
. La présente invention concerne des dérivés benzylidéniques, leur, préparation et leur application en thérapeutique.. The present invention relates to benzylidenic derivatives, their preparation and their therapeutic use.
Les composés de 1‘invention répondent à la formule (I) NR.R.The compounds of the invention correspond to formula (I) NR.R.
^ C = N - CH - COR.^ C = N - CH - COR.
dans laquelle n et m sont indépendamment l'un de l'autre 1,2 ou 3, 10 R^ est un atome d'hydrogène ou d'halogène, R2 est un atome d'hydrogène ou d'halogène, R3 et sont indépendamment l'un de l'autre un atome d'hydrogène, un radical alkyle ou acyle, Rÿ est un atome d'hydrogène ou un radical alkyle, 15 Rg est un groupe amino, alkylamino, dialky.'.amino, hydroxy- alkylamino/ ou un hétérocycle azoté pouvant comporter un autre hétéroatome et/ou pouvant porter un radical alkyle, les radicaux alkyles ayant de 1 à 4 atomes de carbone.in which n and m are independently of each other 1,2 or 3, 10 R ^ is a hydrogen or halogen atom, R2 is a hydrogen or halogen atom, R3 and are independently from each other a hydrogen atom, an alkyl or acyl radical, Rÿ is a hydrogen atom or an alkyl radical, Rg is an amino, alkylamino, dialky. amino, hydroxyalkylamino group or a nitrogen heterocycle which may contain another heteroatom and / or which may carry an alkyl radical, the alkyl radicals having from 1 to 4 carbon atoms.
Λ Un groupe de composés préférés de l'invention est formé par 20 ceux dans lesquels R est un atome de chlore en position 5 et R2 est H ou un atome d'halogène.Λ A group of preferred compounds of the invention is formed by those in which R is a chlorine atom in position 5 and R2 is H or a halogen atom.
Dans ce groupe les composés de choix sont ceux dans lequels R- et R. sont H, Rc est H et R. est NH~.In this group, the compounds of choice are those in which R- and R. are H, Rc is H and R. is NH ~.
3 4 - 5 6 2 ! Les composés de l'invention peuvent exister sous les 2 formes I 25 stéréochimiques syn et anti 1 / ·*- 2 >WR R NR_R.3 4 - 5 6 2! The compounds of the invention can exist in the 2 stereochemical forms I syn and anti 1 / · * - 2> WR R NR_R.
-’·ίζ Λ"' ",,H0C .·.· .- ’· ίζ Λ" '",, H0C. ·. ·.
,,-ό Γ. ' 5 syn anti,, - ό Γ. '5 syn anti
En général, la séparation est effectuée par cristallisations fractionnées.In general, the separation is carried out by fractional crystallizations.
vv
Les composés intermédiaires' hydroxylés (III) peuvent également exister sous les 2 formes syn et anti, 10 Par ailleurs, les composés dans lescruels est un radical > b alkyle peuvent exister sous la forme de racémate ou d'énantiomères qui font partie de l'invention.The hydroxylated intermediate compounds (III) can also exist in the 2 syn and anti forms, 10 Furthermore, the compounds in the cruel is a radical> b alkyl can exist in the form of racemate or enantiomers which are part of the invention.
Selon l'invention on peut préparer les composés (I) selon le schéma réactionnel suivant : À ο b 3According to the invention, the compounds (I) can be prepared according to the following reaction scheme: À ο b 3
Schéma : NR3R4Schematic: NR3R4
(Rl>n-^lj^ + H2N - CH2 - CH20H(Rl> n- ^ lj ^ + H2N - CH2 - CH20H
Jx, (II)Jx, (II)
’R2'm I'R2'm I
· * * Ψ· * * Ψ
Nr3R4Nr3R4
(r.) _L I(r.) _L I
ln-- = N - ch2 - ch2oh ;ni) (R.)--| + H_N - CH - CORc (IV) 2 m JJ 2 j 6 R5 Φ <Vn—\- | = N - CH - C0R^ I 6 (A *5 (Vm-- (I,ln-- = N - ch2 - ch2oh; ni) (R.) - | + H_N - CH - CORc (IV) 2 m DD 2 d 6 R5 Φ <Vn - \ - | = N - CH - C0R ^ I 6 (A * 5 (Vm-- (I,
(U(U
44
Les benzophénones de départ (II) sont connues.The starting benzophenones (II) are known.
Les composés aminés (IV) sont connus.Amino compounds (IV) are known.
La réactiôn de la benzophénone (II) avec l'éthanol-amine est effectuée à une température de 100 à 140°C.The reaction of benzophenone (II) with ethanol-amine is carried out at a temperature of 100 to 140 ° C.
5 La réaction entre le composé intermédiaire hydroxylê (III) et le composé aminé H-N-CH-COR.. (IV) éventuellement sous ·5 The reaction between the hydroxylated intermediate compound (III) and the amino compound H-N-CH-COR .. (IV) possibly under ·
Δ \ OΔ \ O
forme .de chlorhydrate, est effectuée à .une température -de , 20 à 150°C, dans un solvant polaire protique ou aprotique 10 tel que le méthanol, l'éthanol, le DMSO ou le DMF.form of hydrochloride, is carried out at a temperature of 20 to 150 ° C in a polar protic or aprotic solvent such as methanol, ethanol, DMSO or DMF.
Par ailleurs les composés dans lesquels R- est H et R. est un - -1 3 4 radical acyle pouvant être obtenus ä partir des composés (I) correspondants dans lesquels R3 et R^ sont H,par acylation dans de la pyridine, par exemple. 1Furthermore, the compounds in which R- is H and R. is a - -1 3 4 acyl radical obtainable from the corresponding compounds (I) in which R3 and R ^ are H, by acylation in pyridine, by example. 1
Les exemples suivants illustrent l’invention.The following examples illustrate the invention.
Les analyses et les spectres IR et RMN ont confirmé la structure des composés.The analyzes and the IR and NMR spectra confirmed the structure of the compounds.
DMSO = diméthylsuifoxyde. DMF = diméthylformamideDMSO = dimethyl sulfoxide. DMF = dimethylformamide
Dans le tableau (I) sont représentés les composés de l'inven-’ 20 tion préparés à titre d'exemples.In Table (I) are shown the compounds of the invention prepared by way of examples.
Les points de fusion marqués d'un astérisque ont été mesurés par analyse thermique différentielle.The melting points marked with an asterisk were measured by differential thermal analysis.
5 EXEMPLE 1 n-(°^ -phényl amino-2 chloro-5 benzylidënyl)- amino-2 acétamide.EXAMPLE 1 n- (2-Phenyl-2-amino-5-chloro-benzylidenyl) -2-aminoacetamide.
Jrj« Cl-5, R2=R3=R4=R5= H, Rg= NH2 JJrj "Cl-5, R2 = R3 = R4 = R5 = H, Rg = NH2 J
formes syn et anti 5 1. N-(fc( -phényl amino-2 chloro-5 benzylidënyl) amino-2 éthanol.syn and anti forms 5 1. N- (fc (-phenyl-amino-2-chloro-5 benzylidenyl) amino-2 ethanol.
On chauffe à 135°C, sous atmosphère inerte, 30g d'amino-2 chloro-5 benzophénone dans 85 ml d ' éthanolamine tout en agitant pendant 4 h. Après refroidissement on verse le mélange réactionnel dans 1,5 1 d’eau. On extrait l'huile formée avec du chloroforme^ 10 La phase organique est lavée 4 fois avec de l’eau, séchée sur MgSO^, filtrée et évaporée jusqu'à cristallisation.Heated to 135 ° C, under an inert atmosphere, 30g of 2-amino-5-chloro-benzophenone in 85 ml of ethanolamine while stirring for 4 h. After cooling, the reaction mixture is poured into 1.5 l of water. The oil formed is extracted with chloroform ^ 10 The organic phase is washed 4 times with water, dried over MgSO ^, filtered and evaporated until crystallization.
On filtre le produit et le fait recristalliser dans du chloroforme. Après filtration, 3 lavages successifs avec de 1.’éther.ret séchage dans un dessicateur on obtient un produit fondant à 15 128°C.The product is filtered and recrystallized from chloroform. After filtration, 3 successive washes with 1. ether. Drying in a desiccator a product melting at 15 128 ° C. is obtained.
Ce produit est sous la forme anti.This product is in the anti form.
2. N-(o(-phényl amino-2 chloro-5 benzylidënyl) amino-2 acétamide.2. N- (o (-phenyl-amino-2-chloro-5 benzylidényl) amino-2 acetamide.
On dissout 33 g de chlorhydrate du glycinamide dans 300 ml de DMSO et on dissout alors dans cette solution 27,4 g de N-(°^-20 phényl amino-2 chloro-5 benzylidënyl)-amino-2 éthanol. On chauffe le mélange à 60°C pendant 6 neures et on le verse dans 4 1 d’eau. On extrait 4 fois avec 500 ml de chloroforme. On * réunit les phaêes organiques, les lave avec 4 fois 1 1 d'eau, sèche sur MgSO^,filtre et évapore à siccité.33 g of glycinamide hydrochloride are dissolved in 300 ml of DMSO and 27.4 g of N- (2-phenyl-2-amino-5-chloro-benzylidenyl) -2-amino ethanol are then dissolved in this solution. The mixture is heated at 60 ° C for 6 hours and poured into 4 1 of water. Extraction is carried out 4 times with 500 ml of chloroform. The organic phages are combined, washed with 4 times 1 l of water, dried over MgSO 4, filtered and evaporated to dryness.
25 On lave le solide obtenu 3 fois avec de l'éther, on le filtre et le sèche dans un dessicateur.The solid obtained is washed 3 times with ether, filtered and dried in a desiccator.
On obtient le mélange des deux formes syn et anti.We obtain the mixture of the two syn and anti forms.
-Par recristallisation dans un mélange mëthanol/éther, on ob-; tient le composé syn.- By recrystallization from a methanol / ether mixture, one obtains; holds the syn compound.
« 6"6
On evaooiß à siccité les eaux de recristallisation. On obtient un solide que l'on recristallise dans de l'éthanol. C'est le composé i*nti.The recrystallization waters are drained to dryness. A solid is obtained which is recrystallized from ethanol. It is the compound i * nti.
Le composé syn fond à 180°C avec décomposition (mesure effec-5 tuée par analyse thermique différentielle).The syn compound melts at 180 ° C with decomposition (measure effec-5 killed by differential thermal analysis).
Le composé anti fond à 143,5°C puis à 177°C (mesure effectuée . par analyse thermique différentielle).The anti-melting compound at 143.5 ° C. then at 177 ° C. (measurement carried out by differential thermal analysis).
Ces mesures montrent que le composé anti se transforme en composé r*yn par chauffage.These measurements show that the anti compound is transformed into compound r * yn by heating.
10 EXEMPLE ^ N- (o( -phényl amino-2 chloro-5 benzylidényl)- amino-2 méthyl-2 acétamide (forme anti-racémate)EXAMPLE ^ N- (o (-phenyl-2-amino-5-chloro-benzylidenyl) - 2-amino-2-methyl-acetamide (anti-racemate form)
= Cl-5, R2=R3=R4= R, R5 = CH3, .Rg = NH2J= Cl-5, R2 = R3 = R4 = R, R5 = CH3, .Rg = NH2J
On chaufîV, ?. 60°C, 17,6 g (0,1413 mole) de chlorhydrate de dl-aianiuamide et 12,95 g (0,0471 mole) de N-(o^-phényl amino-15 2 chlorc-5 benzylidényl)-amino-2 éthanol sous forme anti dans 80 ml de DMSO, pendant 10 heures* jusqu'à 70eC pendant 16 heures; puis à i?'°C pendant 16 heures et à 90°C pendant 8 heures.We heat,?. 60 ° C, 17.6 g (0.1413 mole) dl-aianiuamide hydrochloride and 12.95 g (0.0471 mole) N- (o ^ -phenyl amino-15 2 chlorc-5 benzylidenyl) -amino -2 ethanol in anti form in 80 ml of DMSO, for 10 hours * up to 70 ° C. for 16 hours; then at 16 ° C for 16 hours and at 90 ° C for 8 hours.
On verse alors le mélange réactionnel dans 2,5 1 d'eau, lentement eu agitant ; on laisse cristalliser l'insoluble puis 20 l'essore le lave à l'eau puis le sèche rapidement sur * à froid.The reaction mixture is then poured into 2.5 l of water, slowly stirring; the insoluble material is left to crystallize and then wrung out, washed with water and then quickly dried on cold.
C'est ur solide jaune collant.It is a sticky yellow solid.
On agite le composé dans environ 100 ml d'éther froid puis filtre l'insoluble fin, le rince avec de petites quantités de 25 ce même solvant froid puis le sèche sous vide à la température ordinaire. C'est un solide beige très clair.The compound is stirred in approximately 100 ml of cold ether and then the fine insoluble material is filtered, rinsed with small amounts of this same cold solvent and then dried under vacuum at ordinary temperature. It is a very light beige solid.
On le dissout à chaud dans de l'éther isopropylique et une quantit' minimum d'acétate d'éthyle ; on filtre une résine, puis ia'-sse le solide recristalliser une nuit au réfrigéra-30 teur ; '' essore, lave et sèche (40°C sur P2°5 et sous vide) .It is dissolved hot in isopropyl ether and a minimum quantity of ethyl acetate; a resin is filtered, then the solid recrystallizes overnight in the refrigerator; '' wring, wash and dry (40 ° C on P2 ° 5 and vacuum).
F = 143,5-l44°C.Mp 143.5-144 ° C.
/ i 7 Γ~ ο . Ή Π % Ή/ i 7 Γ ~ ο. Ή Π% Ή
CS4JCS4J
U οο α) οο co ιη ι Ο I—I κ ·» » — I in in co ο -er ιη •η ·. r* ο 00 ΙΟ ·<U οο α) οο co ιη ι Ο I — I κ · »» - I in in o er ιη • η ·. r * ο 00 ΙΟ · <
Fm com »-< cs ιπ ι-ι σιFm com "- <cs ιπ ι-ι σι
Γ-ΊτΤ CSΓ-ΊτΤ CS
r—i Ή •H -Η Ο -P Q) +) θ' Ç in tn C ο 0) -Η -Η C » co C ni m ε c -P c +> c «a \\ «ew U >1 C >1 C >t ^ G in rt G o O io d w fQ ’W '2 ^rH «4) >ΊΐΠ t, '-V-' H ω ε ωr — i Ή • H -Η Ο -PQ) +) θ 'Ç in tn C ο 0) -Η -Η C "co C ni m ε c -P c +> c" a \\ "ew U> 1 C> 1 C> t ^ G in rt G o O io dw fQ 'W' 2 ^ rH «4)> ΊΐΠ t, '-V-' H ω ε ω
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υ ε oυ ε o
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fflintN CS W CM CS tcfflintN CS W CM CS tc
U—« Pi vo ta Fa FC FC UU— “Pi vo ta Fa FC FC U
I ~w Di S S 2 53 II ~ w Di S S 2 53 I
^2 oj^ 2 oj
Pi » m 11 /= υ m)--*— / —-\ m * ΑΛ ps ta te te ta fcPi »m 11 / = υ m) - * - / —- \ m * ΑΛ ps ta te te ta fc
§ G§ G
H — ^ ή m ro pi '«r m ta m S'-' dî ta ta u FaH - ^ ή m ro pi '' r m ta m S'- 'dî ta ta u Fa
Μ υ ο OΜ υ ο O
m m K ra Fa ta Fa ia u « cs d: ta ta Fa ta ta !__ ! * I «π m in in in inm m K ra Fa ta Fa ia u “cs d: ta ta Fa ta ta! __! * I "π m in in in in
! Pi I I I I I! Pi I I I I I
I—ΐ i—I rl r-1 r—1 u u u u u «y io o pt »h cs m ^ m ε /! δ 8 in in in ^j·I — ΐ i — I rl r-1 r — 1 u u u u u “y io o pt” h cs m ^ m ε /! δ 8 in in in ^ j ·
·. H·. H
Ή Γ0 CN CN f—( q in vr in co |Ή Γ0 CN CN f— (q in vr in co |
q i—ί i—) i—1 rH LOq i — ί i—) i — 1 rH LO
— litt ιΗ m CN iH ro t, cn ^ in co «4· <—I (—ii—ii—I p—i "- ' ................1 ' - ----------— -- -- litt ιΗ m CN iH ro t, cn ^ in co "4 · <—I (—ii — ii — I p — i" - '................ 1' - ----------— - -
•H• H
0) -P0) -P
m tn d o -h -H -Hm tn d o -h -H -H
g ddin+J 4-> C +>g ddin + J 4-> C +>
U HW Ö G >1 GU HW Ö G> 1 G
q »—! C Ο π$ (ϋ CO fOq "-! C Ο π $ (ϋ CO fO
rj. id) >iin w ε w ro ‘ ï" <5θ i" i"rj. id)> iin w ε w ro ‘ï" <5θ i "i"
MM
in £3 W K K bHin £ 3 W K K bH
& U& U
i pT w « K a ai pT w "K a a
m M K W Km M K W K
Pi < <N ^Pi <<N ^
Pi K ffi S I XPi K ffi S I X
r—tr — t
UU
in m m ld tnin m m ld tn
r—i I I I I Ir — i I I I I I
JV| ·—( 1—l i—l r—l f—lJV | · - (1 — l i — l r — l f — l
U O U U UU O U U U
\o : tn\ o: tn
OO
] a o g io r- co cri .—i] a o g io r- co cri. — i
O -UOR
y 9y 9
Les composés (I) ont été soumis à divers essais pharmacologiques .The compounds (I) have been subjected to various pharmacological tests.
Leur toxicité aiguë déterminée sur des souris CD 1 est » respectivement^1000 mg/kg par voie i.p. et^2000 mg/kg par 5 voie orale.Their acute toxicity, determined in CD 1 mice, is respectively 1000 mg / kg i.p. and ^ 2000 mg / kg orally.
Dans le test de l'antagonisme vis à vis des convulsions induites par la bicuculline chez la souris (Curtis, D.R., et al. Brain Res. 1971, 33, 57 i Worms P. et al., Life Science, 1979, , 25, p. 607) la dose active 50% (DA 50), 10 c'est à dire la dose qui protège 50% des animaux contre les effets de la bicuculline est d'environ 5 mg/kg par voie i.p. et.'varie de 4,5 à 17 mg/kg par voie orale.In the test of antagonism with respect to convulsions induced by bicucullin in mice (Curtis, DR, et al. Brain Res. 1971, 33, 57 i Worms P. et al., Life Science, 1979,, 25 , p. 607) the active dose 50% (DA 50), 10 ie the dose which protects 50% of the animals against the effects of bicuculline is approximately 5 mg / kg by ip route and varies from 4.5 to 17 mg / kg orally.
Dans le test "Eating test" (Stephens R.J., Brit. J. Pharmacol. 1973, £9, 146) les composés sont administrés à différentes 15 dosesf par voie orale chez la souris.In the "Eating test" (Stephens R.J., Brit. J. Pharmacol. 1973, £ 9, 146) the compounds are administered at different doses orally in mice.
Pour chaque dose le pourcentage d'augmentation de la nourriture consommée·:.est déterminée par rapport au contrôle.For each dose the percentage increase in food consumed ·:. Is determined in relation to the control.
Dans le tableau les pourcentages sont indiqués pour différentes doses de composés (I) 20 Dose (mg/kg) % . _P.o·__ 3 + 7 à + 44 10 + 25 à + 68 30 + 20 à + 9i 25 Les essais montrent que les composés de l'invention ont des propriétés anticonvulsivantes et/ou anxiolytiques et peuvent être utilisés pour le traitement des épilepsies, des convulsions et de l'anxiété, par exemple.In the table the percentages are indicated for different doses of compounds (I) 20 Dose (mg / kg)%. _P.o · __ 3 + 7 to + 44 10 + 25 to + 68 30 + 20 to + 9i 25 The tests show that the compounds of the invention have anticonvulsant and / or anxiolytic properties and can be used for the treatment of epilepsies, seizures and anxiety, for example.
y-'· 10 * Les composés peuvent être présentés sous toute forme pharma ceutique en association avec tout excipient approprié pour l'administration par voie orale ou parentérale, par exemple sous la forme de gélules, comprimés, capsules, dragées, solu-5 tions et suspensions .....y- '· 10 * The compounds may be presented in any pharmaceutical pharmaceutical form in combination with any excipient suitable for oral or parenteral administration, for example in the form of capsules, tablets, capsules, dragees, solutions. and suspensions .....
La posologie quotidienne peut aller de 5 à 500 mg.The daily dosage can range from 5 to 500 mg.
ί'Λ \ » tί'Λ \ »t
Claims (2)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR7929139A FR2470116A1 (en) | 1979-11-27 | 1979-11-27 | BENZYLIDENIC DERIVATIVES, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION |
FR7929139 | 1979-11-27 |
Publications (1)
Publication Number | Publication Date |
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LU82958A1 true LU82958A1 (en) | 1982-06-30 |
Family
ID=9232118
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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LU82958A LU82958A1 (en) | 1979-11-27 | 1980-11-26 | BENZYLIDENIC DERIVATIVES, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION |
Country Status (20)
Country | Link |
---|---|
JP (1) | JPS5692852A (en) |
AT (1) | AT372077B (en) |
AU (1) | AU535262B2 (en) |
BE (1) | BE886361A (en) |
CA (1) | CA1145760A (en) |
DE (1) | DE3044542A1 (en) |
DK (1) | DK503180A (en) |
ES (1) | ES497146A0 (en) |
FR (1) | FR2470116A1 (en) |
GB (1) | GB2063867B (en) |
GR (1) | GR72133B (en) |
IL (1) | IL61568A (en) |
IT (1) | IT1134469B (en) |
LU (1) | LU82958A1 (en) |
NL (1) | NL8006427A (en) |
NO (1) | NO803561L (en) |
NZ (1) | NZ195654A (en) |
PT (1) | PT72114B (en) |
SE (1) | SE8008279L (en) |
ZA (1) | ZA807389B (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
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JPS59501313A (en) * | 1982-07-30 | 1984-07-26 | インステイチユ−ト オルガニチエスコゴ シンテザ アカデミイ ナウク ラトビイスコイ エスエスア−ル | Condensation products of α↓-aminoisopropylphenyl ketones in carbonyl C═O bonds with substituted amines or functionally substituted hydrazines or derivatives of naturally occurring amino acids, having antitumor activity |
US5278191A (en) * | 1988-08-31 | 1994-01-11 | G. D. Searle & Co. | Diphenylmethylaminoacetamide derivatives as anti-convulsants |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
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FR1497456A (en) * | 1964-06-15 | 1967-10-13 | Clin Byla Ets | Ortho-amino aryl ketimines, heterocyclic compounds attached to them and preparation of these various bodies |
-
1979
- 1979-11-27 FR FR7929139A patent/FR2470116A1/en active Granted
-
1980
- 1980-11-26 CA CA000365550A patent/CA1145760A/en not_active Expired
- 1980-11-26 IT IT26247/80A patent/IT1134469B/en active
- 1980-11-26 ES ES497146A patent/ES497146A0/en active Granted
- 1980-11-26 JP JP16736380A patent/JPS5692852A/en active Pending
- 1980-11-26 NL NL8006427A patent/NL8006427A/en not_active Application Discontinuation
- 1980-11-26 IL IL61568A patent/IL61568A/en unknown
- 1980-11-26 SE SE8008279A patent/SE8008279L/en not_active Application Discontinuation
- 1980-11-26 BE BE0/202944A patent/BE886361A/en not_active IP Right Cessation
- 1980-11-26 GB GB8037869A patent/GB2063867B/en not_active Expired
- 1980-11-26 DE DE19803044542 patent/DE3044542A1/en not_active Withdrawn
- 1980-11-26 ZA ZA00807389A patent/ZA807389B/en unknown
- 1980-11-26 AT AT0577780A patent/AT372077B/en active
- 1980-11-26 PT PT72114A patent/PT72114B/en unknown
- 1980-11-26 AU AU64730/80A patent/AU535262B2/en not_active Ceased
- 1980-11-26 NZ NZ195654A patent/NZ195654A/en unknown
- 1980-11-26 DK DK503180A patent/DK503180A/en not_active Application Discontinuation
- 1980-11-26 LU LU82958A patent/LU82958A1/en unknown
- 1980-11-26 GR GR63468A patent/GR72133B/el unknown
- 1980-11-26 NO NO803561A patent/NO803561L/en unknown
Also Published As
Publication number | Publication date |
---|---|
DE3044542A1 (en) | 1981-09-03 |
IT1134469B (en) | 1986-08-13 |
GR72133B (en) | 1983-09-19 |
PT72114B (en) | 1981-09-29 |
ES8107168A1 (en) | 1981-10-01 |
IT8026247A0 (en) | 1980-11-26 |
ES497146A0 (en) | 1981-10-01 |
IL61568A (en) | 1984-12-31 |
ZA807389B (en) | 1981-11-25 |
NL8006427A (en) | 1981-07-01 |
CA1145760A (en) | 1983-05-03 |
PT72114A (en) | 1980-12-01 |
AU6473080A (en) | 1981-06-04 |
BE886361A (en) | 1981-05-26 |
NZ195654A (en) | 1982-05-31 |
NO803561L (en) | 1981-05-29 |
DK503180A (en) | 1981-05-28 |
IL61568A0 (en) | 1980-12-31 |
AU535262B2 (en) | 1984-03-08 |
FR2470116A1 (en) | 1981-05-29 |
FR2470116B1 (en) | 1983-07-18 |
AT372077B (en) | 1983-08-25 |
SE8008279L (en) | 1981-05-28 |
GB2063867A (en) | 1981-06-10 |
GB2063867B (en) | 1983-09-14 |
JPS5692852A (en) | 1981-07-27 |
ATA577780A (en) | 1983-01-15 |
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