FR709M - - Google Patents
Info
- Publication number
- FR709M FR709M FR840924A FR840924A FR709M FR 709 M FR709 M FR 709M FR 840924 A FR840924 A FR 840924A FR 840924 A FR840924 A FR 840924A FR 709 M FR709 M FR 709M
- Authority
- FR
- France
- Prior art keywords
- cha
- alpha
- azetidinyl
- hydrochloride
- lidocaine
- 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.)
- Active
Links
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000003589 local anesthetic agent Substances 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 206010002091 Anaesthesia Diseases 0.000 description 5
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 5
- 230000037005 anaesthesia Effects 0.000 description 5
- 229960004194 lidocaine Drugs 0.000 description 5
- 241000700199 Cavia porcellus Species 0.000 description 2
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- RLVVIGIYIMDCAU-UHFFFAOYSA-N 3,3-dimethylazetidine Chemical compound CC1(C)CNC1 RLVVIGIYIMDCAU-UHFFFAOYSA-N 0.000 description 1
- DVPXDZWZLKNLJX-UHFFFAOYSA-N 3,3-dimethylazetidine;hydrochloride Chemical compound Cl.CC1(C)CNC1 DVPXDZWZLKNLJX-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229960003920 cocaine Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- NRPTXWYBRKRZES-UHFFFAOYSA-N n-(2,6-dimethylphenyl)acetamide Chemical compound CC(=O)NC1=C(C)C=CC=C1C NRPTXWYBRKRZES-UHFFFAOYSA-N 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003510 tertiary aliphatic amines Chemical class 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- -1 triethylamine Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
république françaiseFrench Republic
MINISTERE DE L'INDUSTRIEMINISTRY OF INDUSTRY
SERVICE de la PROPRIÉTÉ INDUSTRIELLEINDUSTRIAL PROPERTY SERVICE
BREVET SPÉCIAL DE MÉDICAMENTSPECIAL MEDICINE PATENT
P.y. n° 840.924 Classification internationale :P.y. No. 840.924 International classification:
N° 709 M A 61 k — € 07 dNo. 709 M A 61 k — € 07 d
Alpha-(3,3-diméthyl-l-azétidinyl)-2,6-dimétliylacétanilide. (Invention : Emilio Testa.) Société dite : LEPETIT S. p.Alpha-(3,3-dimethyl-l-azetidinyl)-2,6-dimethylacetanilide. (Invention: Emilio Testa.) Company called: LEPETIT S. p.
A. résidant en Italie.A. residing in Italy.
Demandé le 12 octobre 1960, à 13 heures, à Paris.Requested on October 12, 1960, at 1 p.m., in Paris.
Délivré par arrêté du 31 juillet 1961.Issued by order of July 31, 1961.
(.Bulletin officiel de la Propriété industrielle [B.S.M.], n° 28 de 1961.)(Official Bulletin of Industrial Property [B.S.M.], No. 28 of 1961.)
(.Demande de brevet déposée en Italie le 14 octobre 1959, sous le n° 17.025,(.Patent application filed in Italy on October 14, 1959, under number 17.025,
au nom de la demanderesse.)in the name of the plaintiff.)
La présente invention a pour objet l'alpha-(3,3-diméthyl-1 - azétidinyl) 2,6 - diméthylacétanilide de formule :The subject of the present invention is alpha-(3,3-dimethyl-1 - azetidinyl) 2,6 - dimethylacetanilide of formula:
ch3ch3
II
y"y"
,ch3,ch3
-nhcoch2n. /c,-nhcoch2n. /vs,
v cha 'v cha '
sch3sch3
ch3ch3
Ce composé est très efficace comme anesthésique local.This compound is very effective as a local anesthetic.
Son activité est supérieure à celle de la cocaïne et de la lidocaïne et sa toxicité est suffisamment faible pour permettre son administration aux êtres humains.Its activity is greater than that of cocaine and lidocaine and its toxicity is low enough to allow its administration to humans.
Le tableau suivant donne les résultats d'une comparaison entre 'es doses isodynamiques de l'alpha-(3,3-diinéthyi-l -azétidinyl)-2,6-diméthylacé -tanilide (DAD), et de lidocaïne dans des expériences pratiquées sur des animaux.The following table gives the results of a comparison between isodynamic doses of alpha-(3,3-diinethyi-l -azetidinyl)-2,6-dimethylacetanilide (DAD), and lidocaine in experiments carried out on animals.
TableauPainting
Doses et concentrationsDoses and concentrations
isodynamiquesisodynamic
RapportReport
Lidocaïne /DADLidocaine /DAD
LidocaïneLidocaine
DADD.A.D.
%%
%%
Anesthésie en surface (lapin)Surface anesthesia (rabbit)
11
0,250.25
44
Anesthésie par infiltration (cobaye)Infiltration anesthesia (guinea pig)
11
>: 0,25>: 0.25
44
Anesthésie en masse (cobaye)Mass anesthesia (guinea pig)
6,156.15
2,632.63
2,112.11
Anesthésie extradurale lombo-sacrale (grenouille)Extradural lumbosacral anesthesia (frog)
22
0,50.5
oo 4oo 4
Anesthésie neurale par transmission sciatique-gastrocnemius (grenouille). . .Neural anesthesia by sciatic-gastrocnemius (frog) transmission. . .
0,50.5
0,20.2
2,52.5
Le produit est utilisable de préférence sous la forme de sels d'addition avec les acides minéraux non toxiques. *The product can preferably be used in the form of addition salts with non-toxic mineral acids. *
Les doses peuvent varier suivant l'effet désiré.Doses may vary depending on the desired effect.
Dans tous les cas, ces doses sont très inférieures à celles de la lidocaïne.In all cases, these doses are much lower than those of lidocaine.
Le procédé pour préparer ce composé consiste à ajouter graduellement au chlorhydrate d'une 3,3-diméthyl-azétidine une quantité équimolécu-laire d'alpha-chloroacéto-2,6-xylide en présence d'un excès de 2 équivalents, et de préférence de 3-5 équivalents, d'une aminé aliphatique tertiaire telle que la triéthylamine, dans un solvant organique inerte.The process for preparing this compound consists of gradually adding to the hydrochloride of a 3,3-dimethyl-azetidine an equimolecular quantity of alpha-chloroaceto-2,6-xylide in the presence of an excess of 2 equivalents, and of preferably 3-5 equivalents of a tertiary aliphatic amine such as triethylamine, in an inert organic solvent.
La solution est alors chauffée à 50-80 °C, et filtrée, le solvant est chassé et le résidu est distillé sous vide.The solution is then heated to 50-80°C, and filtered, the solvent is removed and the residue is distilled under vacuum.
L'exemple suivant est donné à titre d'illustration de l'invention.The following example is given by way of illustration of the invention.
Exemple. — A une solution de 41 g de chlorhydrate de 3,3-diméthylazétidine et 93 g de triéthylamine dans 400 cm3 de benzène anhydre, on ajoute graduellement 60 g d'alpha-chloro-acéto-2,6-xylide sous agitation, à la température ambiante.Example. — To a solution of 41 g of 3,3-dimethylazetidine hydrochloride and 93 g of triethylamine in 400 cm3 of anhydrous benzene, 60 g of alpha-chloro-aceto-2,6-xylide are gradually added with stirring, at the ambient temperature.
La solution est alors chauffée à 70 °C environ pendant cinq heures, puis filtrée et évaporée jusqu'à siccité.The solution is then heated to approximately 70°C for five hours, then filtered and evaporated until dryness.
Le résidu est distillé et recueilli à 175-185 °C/0,5 mm.The residue is distilled and collected at 175-185°C/0.5 mm.
Point de fusion : 93-95°; rendement 55 g; chlorhydrate : point de fusion 195-197°.Melting point: 93-95°; yield 55 g; hydrochloride: melting point 195-197°.
RÉSUMÉSUMMARY
La présente invention concerne, à titre de médi-The present invention relates, as a medi-
2 - 413512 - 41351
Prix du fascicule: 2 NFPrice of the booklet: 2 NF
Claims (10)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR840924A FR709M (en) | 1960-10-12 | 1960-10-12 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR840924A FR709M (en) | 1960-10-12 | 1960-10-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| FR709M true FR709M (en) | 1961-07-31 |
Family
ID=88292796
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR840924A Active FR709M (en) | 1960-10-12 | 1960-10-12 |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR709M (en) |
-
1960
- 1960-10-12 FR FR840924A patent/FR709M/fr active Active
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