BE529385A - - Google Patents
Info
- Publication number
- BE529385A BE529385A BE529385DA BE529385A BE 529385 A BE529385 A BE 529385A BE 529385D A BE529385D A BE 529385DA BE 529385 A BE529385 A BE 529385A
- Authority
- BE
- Belgium
- Prior art keywords
- bis
- ether
- oxide
- isopropanol
- diethylamino
- Prior art date
Links
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- -1 aryl radical Chemical class 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 4
- WJMWSPUOZRYMJD-UHFFFAOYSA-N (1-phenylcyclopentyl)methanol Chemical compound C=1C=CC=CC=1C1(CO)CCCC1 WJMWSPUOZRYMJD-UHFFFAOYSA-N 0.000 claims description 2
- UAJVCELPUNHGKE-UHFFFAOYSA-N 1-phenylheptan-1-ol Chemical compound CCCCCCC(O)C1=CC=CC=C1 UAJVCELPUNHGKE-UHFFFAOYSA-N 0.000 claims description 2
- NYLOEXLAXYHOHH-UHFFFAOYSA-N 2,2-diphenylethanol Chemical compound C=1C=CC=CC=1C(CO)C1=CC=CC=C1 NYLOEXLAXYHOHH-UHFFFAOYSA-N 0.000 claims description 2
- QILSFLSDHQAZET-UHFFFAOYSA-N Diphenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N Methyl radical Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000004350 aryl cycloalkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- NZIDEIRWYRJYAI-UHFFFAOYSA-N (1-phenylcyclohexyl)methanol Chemical compound C=1C=CC=CC=1C1(CO)CCCCC1 NZIDEIRWYRJYAI-UHFFFAOYSA-N 0.000 claims 1
- 241001331845 Equus asinus x caballus Species 0.000 claims 1
- HOLAPZNLQDHKQJ-UHFFFAOYSA-N cyclohexyl(thiophen-2-yl)methanol Chemical compound C=1C=CSC=1C(O)C1CCCCC1 HOLAPZNLQDHKQJ-UHFFFAOYSA-N 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- AJYOOHCNOXWTKJ-UHFFFAOYSA-N p-Chlorobenzhydrol Chemical compound C=1C=C(Cl)C=CC=1C(O)C1=CC=CC=C1 AJYOOHCNOXWTKJ-UHFFFAOYSA-N 0.000 claims 1
- UWCWPJZIKQCZIM-UHFFFAOYSA-N (4-chlorophenyl)-cyclohexylmethanol Chemical compound C=1C=C(Cl)C=CC=1C(O)C1CCCCC1 UWCWPJZIKQCZIM-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- QXXHHHWXFHPNOS-UHFFFAOYSA-N 1-phenylcyclohexane-1-carboxylic acid Chemical compound C=1C=CC=CC=1C1(C(=O)O)CCCCC1 QXXHHHWXFHPNOS-UHFFFAOYSA-N 0.000 description 1
- RHPCYZLXNNRRMB-UHFFFAOYSA-N 1-phenylcyclopentane-1-carboxylic acid Chemical compound C=1C=CC=CC=1C1(C(=O)O)CCCC1 RHPCYZLXNNRRMB-UHFFFAOYSA-N 0.000 description 1
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 description 1
- ZYKZPCXHDHXBJP-UHFFFAOYSA-N 2-(diethylamino)propan-2-ol Chemical compound CCN(CC)C(C)(C)O ZYKZPCXHDHXBJP-UHFFFAOYSA-N 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N Sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- BJKLPLABXHXMIM-UHFFFAOYSA-N aluminum;lithium;hydride Chemical compound [H-].[H-].[H-].[H-].[Li+].[Al+3] BJKLPLABXHXMIM-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- QDYKZBKCLHBUHU-UHFFFAOYSA-N cyclohexyl(phenyl)methanol Chemical compound C=1C=CC=CC=1C(O)C1CCCCC1 QDYKZBKCLHBUHU-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- HPQVWDOOUQVBTO-UHFFFAOYSA-N lithium aluminium hydride Substances [Li+].[Al-] HPQVWDOOUQVBTO-UHFFFAOYSA-N 0.000 description 1
- OCZDCIYGECBNKL-UHFFFAOYSA-N lithium;alumanuide Chemical compound [Li+].[AlH4-] OCZDCIYGECBNKL-UHFFFAOYSA-N 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000003170 musculotropic Effects 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002048 spasmolytic Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/34—Monohydroxylic alcohols containing six-membered aromatic rings and other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
<Desc/Clms Page number 1>
Cettains éthers-oxydes du 1.3-bis(diéthylamino)-isopropanol exercent une action spasmolytique musculotrope remarquable tout en ayant une toxicité relativement faible.
Les éthers-oxydes de l'invention répondent à la formule générale
EMI1.1
dans laquelle
R est un atome d'hydrogène ou un radical méthyle
R' est un atome d'hydrogène, un radical cycloalcoyle ou aryle sub- stitué ou non
R" est un radical alcoyle. aryle, cycloalcoyle. aralcoyle. hétéro- cyclique, aryl-cycloalcoyle ou aralcoyl-hétérocyclique.
Ces produits se préparent en faisant réagir un dérivé métallique d'un méthanol substitué avec le 1.3-bis-(diéthylamino)-2-choropropane.
Ce dernier composé s'obtient suivant la méthode décrite par TORIZO TAKASKI et coll. /J.pharh.Soc.Japan. , (1949). 211-12/.
EXEMPLE 1.
Ether-oxyde du cyclohexyl-p-chlorphényl-carbinol et du 1.3-bis-(diéthyl- amino)-isopropanol.
EMI1.2
A une suspension de O.l mole d'amidure de sodium dans 100 cm3 de xylène. on ajoute 0.l mole de cyclohexyl-p-chlorophényl-méthanol et on chauffe à reflux pendant 2 heures.
Au sel sodé ainsi obtenu, on ajoute 0,1 mole de 1.3-bis-(diéthylamino)-2-chloropropane en solution dans 50 cm3 de xylène et on chauffe à reflux pendant 3 heures.
Après refroidissement, on ajoute 100 cm3 d'eau et on décante la solution xylénique qu'on lave encore une fois à l'eau, On sèche la solution xylénique en filtrant sur sulfate de soude. On évapore ensuite solvant sous vide et on fractionne soigneusement le résidu par distillation sous vide poussé (rendt. 75%). On sépare 30 g du produit de P.Ebull.
160 C/0.1 mm Hg.
<Desc/Clms Page number 2>
EXEMPLE 2.
Dans l'exemple suivant, on se sert de dérivés sodés d'alcools connus.-
EMI2.1
Ether-oxyde du benzhydrylméthanol et du 1,3-hïs-,diéthy.-amino)-isoproparol.
EMI2.2
P.Ebull.. 170 C/0.1 mm Hg.
EMI2.3
Ether-oxyde du benzhydrol et du 1,3-b=-id'hylam3.no)--isopropanol.
EMI2.4
P.Ebull. 155 C/0.1 mm Hg.
EMI2.5
Ether-oxyde du p-chlombenzhydrol et du 1.3-bis-(diéthylamino)-isopropanol.
EMI2.6
P.Ebull. 168 C/0.1 mm Hg.
EMI2.7
Ether-oxyde du\4f.Phényl-méthyl-méthanol et du 1,3-bia-(déthylamino)iso- propanol.
EMI2.8
P.Ebull 160 C/0.05 mm Hg.
<Desc/Clms Page number 3>
Ether-oxyde du cyclohexyl-phényl-méthanol et du 1.3-bis-(diéthylamino)-isopropanolo .
EMI3.1
P.Ebull. 155 C/0.1 mm Hg.
Ether-oxyde du phényl-hexyl-méthanol et du 1.3-bis-(diéthyl-amino)-isopro- panol.-
EMI3.2
P.Ebull. 158 C/0.3 mm Hg.
Ether-oxyde du cyclohexyl-2-thlényl-méthanol et du 1.3-bis-(diéthylamino)isopropanol.
EMI3.3
P.Ebull.55 C/0.1 mm Hg.
EXEMPLE 3.
Dans cet exemple on prend, comme matières premières, des al- cools qui n'ont pas été décrits dans la littérature.
Ce sont : - le 1-phényl-cyclopentaneméthanol (P.Ebull. 132-135 C/3 mm Hg) obtenu par réduction du chlorure de l'acide 1-phényl-1-cyclo-pentanecarboxylique au moyen de l'hydrure de lithium-aluminium.
- le 1-phényl-cyclohexaneméthanol (P.Ebull. 118-120 C O.01 mm Hg)obtenu par réduction du chlorure de l'acide 1-phényl-l-cyclohexane carboxylique au moyen de l'hydrure de lithium-aluminium.
- l'alpha-furfuryl-benzylméthanol (P.Ebull. 111 C/0.3 mm Hg) obtenu par ré- duction de l'acide furfuryl-phényl-acétique. au moyen de l'hydrate de 11- thium-aluminium.
<Desc/Clms Page number 4>
Les éthers-oxydes sont :
EMI4.1
Ether-oxyde du 1-phényl-cyclopentaneméthanol et du 1.3-bis-(dléthylamim)- isopropanol.
EMI4.2
EMI4.3
P.Ebull. 160eG/o, 05 zm.Hg.
Ether-oxyde du 1-phérl.-cyclohexanemétharol et du .,3 bis-(diêthylami)- isopropanol.
EMI4.4
EMI4.5
P.Ebull. 155-16 C/Q; J5 mm Hg.
Ether-oxyde de lalpha-furfulyl-benzylmojaool et du 1,3-bis-(diéthylenino)- isopropanol.
EMI4.6
EMI4.7
P.Ebull. 165 r3.- mm ig.
RESUME.
1 Ethers-oxydes du 1,3-bia-(diéthylamino)-isopropanol répondant à la for-
<Desc / Clms Page number 1>
These 1.3-bis (diethylamino) -isopropanol ethers-oxides exert a remarkable musculotropic spasmolytic action while having relatively low toxicity.
The ethers-oxides of the invention correspond to the general formula
EMI1.1
in which
R is a hydrogen atom or a methyl radical
R 'is a hydrogen atom, a cycloalkyl or aryl radical, substituted or not
R "is an alkyl, aryl, cycloalkyl, aralkyl, heterocyclic, aryl-cycloalkyl or aralkyl-heterocyclic radical.
These products are prepared by reacting a metal derivative of a substituted methanol with 1.3-bis- (diethylamino) -2-choropropane.
The latter compound is obtained according to the method described by TORIZO TAKASKI et al. /J.pharh.Soc.Japan. , (1949). 211-12 /.
EXAMPLE 1.
Ether-oxide of cyclohexyl-p-chlorphenyl-carbinol and 1,3-bis- (diethylamino) -isopropanol.
EMI1.2
Has a suspension of 0.1 mole of sodium amide in 100 cm3 of xylene. 0.1 mole of cyclohexyl-p-chlorophenyl-methanol is added and the mixture is heated at reflux for 2 hours.
To the sodium salt thus obtained, 0.1 mole of 1.3-bis- (diethylamino) -2-chloropropane dissolved in 50 cm3 of xylene is added and the mixture is refluxed for 3 hours.
After cooling, 100 cm3 of water are added and the xylenic solution is decanted, which is washed again with water, the xylenic solution is dried by filtering over sodium sulfate. The solvent is then evaporated off in vacuo and the residue is carefully fractionated by distillation under high vacuum (yield 75%). 30 g of the product of P.Ebull are separated.
160 C / 0.1 mm Hg.
<Desc / Clms Page number 2>
EXAMPLE 2.
In the following example, sodium derivatives of known alcohols are used.
EMI2.1
Ether-oxide of benzhydrylmethanol and 1,3-his-, diethyl.-amino) -isoproparol.
EMI2.2
P.Ebull .. 170 C / 0.1 mm Hg.
EMI2.3
Ether-oxide of benzhydrol and 1,3-b = -id'hylam3.no) - isopropanol.
EMI2.4
P.Ebull. 155 C / 0.1 mm Hg.
EMI2.5
Ether-oxide of p-chlombenzhydrol and 1.3-bis- (diethylamino) -isopropanol.
EMI2.6
P.Ebull. 168 C / 0.1 mm Hg.
EMI2.7
Phenyl-methyl-methanol ether-oxide and 1,3-bia- (ethylamino) isopropanol.
EMI2.8
P.Ebull 160 C / 0.05 mm Hg.
<Desc / Clms Page number 3>
Ether-oxide of cyclohexyl-phenyl-methanol and of 1.3-bis- (diethylamino) -isopropanolo.
EMI3.1
P.Ebull. 155 C / 0.1 mm Hg.
Ether-oxide of phenyl-hexyl-methanol and of 1.3-bis- (diethyl-amino) -isopro-panol.-
EMI3.2
P.Ebull. 158 C / 0.3 mm Hg.
Ether-oxide of cyclohexyl-2-thlényl-methanol and 1.3-bis- (diethylamino) isopropanol.
EMI3.3
P.Ebull. 55 C / 0.1 mm Hg.
EXAMPLE 3.
In this example, alcohols which have not been described in the literature are taken as raw materials.
These are: - 1-phenyl-cyclopentanemethanol (P.Ebull. 132-135 C / 3 mm Hg) obtained by reduction of the chloride of 1-phenyl-1-cyclo-pentanecarboxylic acid by means of lithium hydride -aluminum.
- 1-phenyl-cyclohexanemethanol (P.Ebull. 118-120 C O.01 mm Hg) obtained by reduction of the chloride of 1-phenyl-l-cyclohexane carboxylic acid by means of lithium aluminum hydride.
- alpha-furfuryl-benzylmethanol (P.Ebull. 111 C / 0.3 mm Hg) obtained by reduction of furfuryl-phenyl-acetic acid. using 11-thium-aluminum hydrate.
<Desc / Clms Page number 4>
The ethers-oxides are:
EMI4.1
Ether-oxide of 1-phenyl-cyclopentanemethanol and 1.3-bis- (dlethylamim) - isopropanol.
EMI4.2
EMI4.3
P.Ebull. 160eG / o, 05 zm.Hg.
Ether-oxide of 1-pherl.-cyclohexanemetharol and., 3 bis- (diethylami) - isopropanol.
EMI4.4
EMI4.5
P.Ebull. 155-16 C / Q; J5 mm Hg.
Alpha-furfulyl-benzylmojaool and 1,3-bis- (diethylenino) - isopropanol ether-oxide.
EMI4.6
EMI4.7
P.Ebull. 165 r3.- mm ig.
ABSTRACT.
1 Ethers-oxides of 1,3-bia- (diethylamino) -isopropanol corresponding to the
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE529385A true BE529385A (en) |
Family
ID=162382
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE529385D BE529385A (en) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE529385A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3254083A (en) * | 1959-05-02 | 1966-05-31 | Boehringer & Soehne Gmbh | [1-(monocarbocyclic aryl)-cycloalkyl]-[(tertiaryamino)-lower alkyl] ethers |
-
0
- BE BE529385D patent/BE529385A/fr unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3254083A (en) * | 1959-05-02 | 1966-05-31 | Boehringer & Soehne Gmbh | [1-(monocarbocyclic aryl)-cycloalkyl]-[(tertiaryamino)-lower alkyl] ethers |
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