CH355446A - Process for preparing dicarbamates - Google Patents
Process for preparing dicarbamatesInfo
- Publication number
- CH355446A CH355446A CH355446DA CH355446A CH 355446 A CH355446 A CH 355446A CH 355446D A CH355446D A CH 355446DA CH 355446 A CH355446 A CH 355446A
- Authority
- CH
- Switzerland
- Prior art keywords
- diol
- butyl
- propanediol
- methyl
- propan
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 238000000034 method Methods 0.000 claims description 21
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
- 150000002009 diols Chemical class 0.000 claims description 12
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 6
- 229940035437 1,3-propanediol Drugs 0.000 claims description 5
- RLFWWDJHLFCNIJ-UHFFFAOYSA-N Aminoantipyrine Natural products CN1C(C)=C(N)C(=O)N1C1=CC=CC=C1 RLFWWDJHLFCNIJ-UHFFFAOYSA-N 0.000 claims description 5
- VEQOALNAAJBPNY-UHFFFAOYSA-N antipyrine Chemical compound CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 claims description 5
- 229960005222 phenazone Drugs 0.000 claims description 5
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 5
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 4
- SIMYRXPCIUXDGR-UHFFFAOYSA-N 2-butylpropane-1,3-diol Chemical compound CCCCC(CO)CO SIMYRXPCIUXDGR-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- BKKAVOLVYULZEM-UHFFFAOYSA-N 2-(2-methylpropyl)propane-1,3-diol Chemical compound CC(C)CC(CO)CO BKKAVOLVYULZEM-UHFFFAOYSA-N 0.000 claims description 2
- DIAKBGLNNAQLNA-UHFFFAOYSA-N 2-pentan-2-ylpropane-1,3-diol Chemical compound CCCC(C)C(CO)CO DIAKBGLNNAQLNA-UHFFFAOYSA-N 0.000 claims description 2
- FZHZPYGRGQZBCV-UHFFFAOYSA-N 2-propylpropane-1,3-diol Chemical compound CCCC(CO)CO FZHZPYGRGQZBCV-UHFFFAOYSA-N 0.000 claims description 2
- OFHQHVCVSKOCCH-UHFFFAOYSA-N 3-carbamoyloxypropyl carbamate Chemical group NC(=O)OCCCOC(N)=O OFHQHVCVSKOCCH-UHFFFAOYSA-N 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 5
- QOOXGUCQYVVEFD-UHFFFAOYSA-N 2-butyl-2-methylpropane-1,3-diol Chemical compound CCCCC(C)(CO)CO QOOXGUCQYVVEFD-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- -1 methyl isobutyl Chemical group 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical group C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 235000020075 ouzo Nutrition 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- QPIAAQDLOJNQMP-UHFFFAOYSA-N 2-ethyl-2-propylpropane-1,3-diol Chemical compound CCCC(CC)(CO)CO QPIAAQDLOJNQMP-UHFFFAOYSA-N 0.000 description 1
- REQVMPVOKUHDOZ-UHFFFAOYSA-N 2-methyl-2-(2-methylpropyl)propane-1,3-diol Chemical compound CC(C)CC(C)(CO)CO REQVMPVOKUHDOZ-UHFFFAOYSA-N 0.000 description 1
- JVZZUPJFERSVRN-UHFFFAOYSA-N 2-methyl-2-propylpropane-1,3-diol Chemical compound CCCC(C)(CO)CO JVZZUPJFERSVRN-UHFFFAOYSA-N 0.000 description 1
- PESGUTZAXXQWJP-UHFFFAOYSA-N 4-methylhexane-1,3-diol Chemical compound CCC(C)C(O)CCO PESGUTZAXXQWJP-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- XBSXQOUEVBSXEI-UHFFFAOYSA-N [2-(carbamoyloxymethyl)-2-ethylpentyl] carbamate Chemical compound NC(=O)OCC(CC)(CCC)COC(N)=O XBSXQOUEVBSXEI-UHFFFAOYSA-N 0.000 description 1
- PCLRAGNZCNZQCA-UHFFFAOYSA-N [2-(carbamoyloxymethyl)-2-methylhexyl] carbamate Chemical compound CCCCC(C)(COC(N)=O)COC(N)=O PCLRAGNZCNZQCA-UHFFFAOYSA-N 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 229940124575 antispasmodic agent Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- ZEYZKQUPVUMZKV-UHFFFAOYSA-N dichloro carbonate Chemical compound ClOC(=O)OCl ZEYZKQUPVUMZKV-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- AVIYEYCFMVPYST-UHFFFAOYSA-N hexane-1,3-diol Chemical compound CCCC(O)CCO AVIYEYCFMVPYST-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical class CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Procédé de préparation de dicarbamates
La présente invention a pour objet un procédé de préparation de nouveaux composés organiques possédant des propriétés antispasmodiques énergi- ques ; ce sont, par exemple : les dicarbamates de
2-n-propyl-1, 3-propane-diol,
2-tert.-butyl-1,3-propane-diol, 2-sec.-butyl-1, 3-propane-diol,
2-n-amyl-1, 3-p, ropane-diol,
2-(1-méthyl-butyl)-1, 3-propane-diol, 2-iso-butyl-1, 3-propane-diol,
2-n-butyl-1, 3-propane-diol,
2-méthyl-2-n-butyl-1, 3-propane-diol,
2-méthyl-2-isobutyl-1, 3-propane-diol,
2-méthyl-2-n-amyl-1, 3-propane-diol, 2-éthyl-2-n-propyl-1, 3-propane-diol.
Ces dicarbamates de 1,3-propane-diol substitués sont des solides cristallisés blancs solubles dans la plupart des solvants organiques, peu solubles dans l'eau aux températures ambiantes ordinaires. Par ébullition en milieu acide ou alcalin, ils s'hydrolysent avec formation du diol correspondant, d'ammoniaque et d'anhydride carbonique.
L'invention a pour objet un procédé pour la préparation de dicarbamates de 1,3-propane-diol substitués en position 2, par réaction d'un 1,3-propanediol substitué en position 2 avec du phosgène, de manière à former le dichlorocarbonate correspondant puis en traitant ce composé avec de l'ammoniaque.
La première étape du procédé peut tre favorisée, par la présence dans le milieu réactionnel, d'un agent de fixation d'acide tel que l'antipyrine, la diméthyl- aniline ou l'hydroxyde de sodium. L'ammoniaque utilisé dans la seconde étape peut tre anhydre ou aqueux.
Les 1,3-propane-diols substitués utilisés dans la fabrication des dicarbamates correspondants peuvent tre préparés par un procédé quelconque connu tel que par réduction de l'ester malonique correspon-
Tableau I 1,3-p, ropanewdiols substitués en position 2
EMI1.1
Point Point ébullition Carbone /o Hydrogène /o
R R'fusion o C oC (rmn) Formule Calculé Trouvé Calculé Trouvé
Htert.-butyle59-61-CHigOg63, 6063, 7712, 2011, 91
H n-amyle-100-106 (0,2) CgHi8O2 65, 73 65, 72 12, 41 11, 93
H l-méthyl-butyle 98-100 (0,5) C8Hj802 65, 73 65, 82 12, 41 11, 90 méthyle isobutyle 26-27 87-92 (0,3) C8H18O2 65, 73 64, 99 12, 41 12, 44 méthyle n-amyle 51-52, 50 ¯ CgH2002 67, 45 67, 34 12, 58 12,
32
éthyle n-propyGe 37 39 115-117 (0,5) C8Hl802 65, 73 65, 34 12, 41 11, 97
Hisobutyle-82-86 (0,3) C7H1602 63, 60 64, 49 12, 20 11, 63 dant. Ce procédé est, par exemple, décrit par
Adkins, J. A. C. S., 70,3125 (1948), décrivant la préparation du n-propyl-1, 3-propane-diol (point d ? ébullition 96-980 C sous 0,4 mm) et du 2-n-butyl1,3-propane-diol (point d'ébullition 98-100 C sous 2 mm), par Mozingo, J. A. C. S., 70,227 (1948), décrivant la préparation du sec.-butyl-1, 3-propane- diol (point d'ébullition 92-105o C sous 0,5 mm), et par Yale, J. A. C.
S., 72,3717 (1950), décrivant la préparation du 2-méthyl-2-n-butyl-1, 3-propane-diol (point d'ébullition 116-1170C sous 0,5mm).
Le tableau I donne les résultats analytiques de quelques propane-diols utilisables comme matière de départ dans le procédé selon l'invention.
Exemple 1
Dicarbamate
de 2-methyl-2-n-butyl-1, 3-propane-diol
A une solution de 100 g de phosgène dans 900 cc de toluène anhydre on ajoute progressivement en agitant 73 g de 2-méthyl-2-n-butyl-1, 3-propanediol. On agite le mélange réaotionnel jusqu'à obtention d'une solution limpide. On ajoute 380 g d'anti- pyrine dissous dans le minimum possible de chloroforme au mélange réactionnel, progressivement et en refroidissant de manière à maintenir la tempéra ture à environ 250 C. Le chlorhydrate d'antipyrine forme se sépare et le mélange réactionnel est agité jusqu'à ce que la réaction soit complète.
On enlevé par filtration le chlorhydrate d'antipyrine solide et on sature le filtrat d'ammoniaque en agitant et refroidissant. On enlève le solide formé au cours du trai tement par l'ammoniaque par filtration, on le sèche et on l'épuise à l'aide d'eau froide, ce qui laisse un résidu de produit de réaction brut. On le purifie par recristallisation au sein d'isopropanol aqueux. On obtient le dicarbamate de 2-méthyl-2-n-butyl-1, 3 propane-diol purifié avec un rendement de 60 ouzo sous forme d'un solide cristallisé blanc possédant les propriétés physiques et les constantes analytiques données dans le tableau II.
Exemple 2
Dicarbamate de 2-ethyl-2-n-propyl-1, 3-propane-diol
On fait réagir 73 g de 2-méthyl-2-n-propyl-1, 3 propane-diol et 100 g de phosgène dans 900 cc de toluène anhydre, comme il est décrit dans l'exemple 1. On purifie le produit brut par recristallisation au sein d'isopropanol aqueux à 15 /o (vol./vol.). On obtient 98 g de produit purifié (62 zozo du rendement théorique) fondant à 115-117 C.
Dans le tableau II suivant, on a donné quelques constantes physiques de dicarbamates de 1,3-pro pane-diols substitués en position 2.
Tableau II
Dicarbamates de 1,3-propane-dnol substitué en position 2
EMI2.1
Azote ouzo
R R'Point fusion oC Formule Calculé Trouvé
H n-propyle 118-120 C8Hl, ; N204 13, 72 13, 40
H tert.-butyle 109-111 CgHt8N204 12, 83 12, 57
H sec.-butyle 113-115 C9H18N204 12, 83 12, 90
H 7z-amyle 131-132 CloH2oN204 12, 06 12, 53
H l-méthyl-butyle 113-115 CloH2oN204 12, 06 11, 94 méthyl n-butyle 112-113 CloH2oN204 12, 06 11, 99 méthyl isobutyle 77-79 CloH2oN204 12, 06 12, 09 méthylK-amyle94-96CnHNaO11, 3711, 25 éthyle n-propyle 115-117 CloH2oO4N2 12, 06 12, 14
H isobutyle 145-146, 5 C9H1SN204 12, 83 12,
77
H n-butyle 137, 5-138,5 CH1aN204 12, 83 12,91
Comme on Fa dit, les dicarbamates préparés par le procédé selon l'invention constituent des agents antispasmodiques efficaces. Essayés sur des animaux d'expérience appropriés, tels que la souris, ils montrent qu'ils protègent efficacement contre les attaques survenant au cours de l'électrochoc.
Les composés obtenus par le procédé selon l'in- vention sont principalement destinés à l'administra- tion par voie orale et se mettent sous forme de pilules, de comprimés ou de capsules par les procédés bien connus. On peut les dissoudre dans un n solvant approprié tel qu'un mélange d'eau et de polyéthylène-glycol ; ils donnent alors une solution propre à l'administration par injection ou par voie rectale.
Process for preparing dicarbamates
The subject of the present invention is a process for the preparation of new organic compounds having strong antispasmodic properties; these are, for example: dicarbamates of
2-n-propyl-1, 3-propan-diol,
2-tert.-butyl-1,3-propan-diol, 2-sec.-butyl-1, 3-propan-diol,
2-n-amyl-1, 3-p, ropan-diol,
2- (1-methyl-butyl) -1, 3-propan-diol, 2-iso-butyl-1, 3-propan-diol,
2-n-butyl-1, 3-propan-diol,
2-methyl-2-n-butyl-1, 3-propan-diol,
2-methyl-2-isobutyl-1, 3-propan-diol,
2-methyl-2-n-amyl-1, 3-propan-diol, 2-ethyl-2-n-propyl-1, 3-propan-diol.
These substituted 1,3-propanediol dicarbamates are white crystalline solids soluble in most organic solvents, poorly soluble in water at ordinary ambient temperatures. By boiling in an acid or alkaline medium, they hydrolyze with the formation of the corresponding diol, ammonia and carbon dioxide.
The invention relates to a process for the preparation of dicarbamates of 1,3-propanediol substituted in position 2, by reaction of a 1,3-propanediol substituted in position 2 with phosgene, so as to form dichlorocarbonate corresponding and then treating this compound with ammonia.
The first step of the process can be favored, by the presence in the reaction medium, of an acid binding agent such as antipyrine, dimethylaniline or sodium hydroxide. The ammonia used in the second stage can be anhydrous or aqueous.
The substituted 1,3-propanediols used in the manufacture of the corresponding dicarbamates can be prepared by any known process such as by reduction of the corresponding malonic ester.
Table I 1,3-p, ropanewdiols substituted in position 2
EMI1.1
Point Boiling point Carbon / o Hydrogen / o
R R'fusion o C oC (rmn) Formula Calculated Found Calculated Found
Htert.-Butyl59-61-CHigOg63, 6063, 7712, 2011, 91
H n-amyl-100-106 (0.2) CgHi8O2 65, 73 65, 72 12, 41 11, 93
H 1-methyl-butyl 98-100 (0.5) C8Hj802 65, 73 65, 82 12, 41 11, 90 methyl isobutyl 26-27 87-92 (0.3) C8H18O2 65, 73 64, 99 12, 41 12, 44 methyl n-amyl 51-52, 50 ¯ CgH2002 67, 45 67, 34 12, 58 12,
32
ethyl n-propyGe 37 39 115-117 (0.5) C8Hl802 65, 73 65, 34 12, 41 11, 97
Hisobutyl-82-86 (0.3) C7H1602 63, 60 64, 49 12, 20 11, 63 before. This process is, for example, described by
Adkins, JACS, 70.3125 (1948), describing the preparation of n-propyl-1,3-propanediol (boiling point 96-980 C at 0.4 mm) and 2-n-butyl1,3 -propan-diol (boiling point 98-100 C under 2 mm), by Mozingo, JACS, 70,227 (1948), describing the preparation of sec-butyl-1, 3-propan-diol (boiling point 92 -105o C under 0.5mm), and by Yale, JAC
S., 72,3717 (1950), describing the preparation of 2-methyl-2-n-butyl-1, 3-propan-diol (boiling point 116-1170C under 0.5mm).
Table I gives the analytical results of some propanediols which can be used as starting material in the process according to the invention.
Example 1
Dicarbamate
2-methyl-2-n-butyl-1, 3-propan-diol
To a solution of 100 g of phosgene in 900 cc of anhydrous toluene is gradually added with stirring 73 g of 2-methyl-2-n-butyl-1, 3-propanediol. The reaction mixture is stirred until a clear solution is obtained. 380 g of antipyrine dissolved in as little chloroform as possible are added to the reaction mixture, gradually and while cooling so as to maintain the temperature at about 250 C. The antipyrine hydrochloride formed separates and the reaction mixture is stirred. until the reaction is complete.
The solid antipyrine hydrochloride was removed by filtration and the filtrate was saturated with ammonia with stirring and cooling. The solid formed during the ammonia treatment is removed by filtration, dried and depleted with cold water, leaving a residue of crude reaction product. It is purified by recrystallization from aqueous isopropanol. Purified 2-methyl-2-n-butyl-1, 3 propanediol dicarbamate is obtained in a yield of 60 ouzo in the form of a white crystalline solid having the physical properties and the analytical constants given in Table II.
Example 2
2-ethyl-2-n-propyl-1,3-propanediol dicarbamate
73 g of 2-methyl-2-n-propyl-1,3-propanediol and 100 g of phosgene are reacted in 900 cc of anhydrous toluene, as described in Example 1. The crude product is purified by recrystallization from 15% aqueous isopropanol (vol./vol.). 98 g of purified product (62% of the theoretical yield) are obtained, melting at 115-117 C.
In the following Table II, some physical constants of dicarbamates of 1,3-pro pane-diols substituted in position 2 are given.
Table II
1,3-propane-dnol dicarbamates substituted in position 2
EMI2.1
Nitrogen ouzo
R R 'Melting point oC Formula Calculated Found
H n-propyl 118-120 C8H1,; N204 13, 72 13, 40
H tert.-Butyl 109-111 CgHt8N2O4 12, 83 12, 57
H sec.-butyl 113-115 C9H18N2O4 12, 83 12, 90
H 7z-amyl 131-132 CloH2oN2O4 12, 06 12, 53
H 1-methyl-butyl 113-115 CloH2oN204 12, 06 11, 94 methyl n-butyl 112-113 CloH2oN204 12, 06 11, 99 methyl isobutyl 77-79 CloH2oN204 12, 06 12, 09 methylK-amyle94-96CnHNaO11, 3711, 25 ethyl n-propyl 115-117 CloH2oO4N2 12, 06 12, 14
H isobutyl 145-146.5 C9H1SN204 12, 83 12,
77
H n-butyl 137.5-138.5 CH1aN2O4 12.83 12.91
As stated, the dicarbamates prepared by the process according to the invention constitute effective antispasmodic agents. Tried on appropriate experimental animals, such as mice, they show that they provide effective protection against attacks occurring during electroshock.
The compounds obtained by the process according to the invention are mainly intended for oral administration and are in the form of pills, tablets or capsules by well known processes. They can be dissolved in a suitable solvent such as a mixture of water and polyethylene glycol; they then give a solution suitable for administration by injection or rectally.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US355446XA | 1956-01-13 | 1956-01-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH355446A true CH355446A (en) | 1961-07-15 |
Family
ID=21883357
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH355446D CH355446A (en) | 1956-01-13 | 1957-01-11 | Process for preparing dicarbamates |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH355446A (en) |
-
1957
- 1957-01-11 CH CH355446D patent/CH355446A/en unknown
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