CH294178A - Process for preparing an asymmetric double camphorate. - Google Patents
Process for preparing an asymmetric double camphorate.Info
- Publication number
- CH294178A CH294178A CH294178DA CH294178A CH 294178 A CH294178 A CH 294178A CH 294178D A CH294178D A CH 294178DA CH 294178 A CH294178 A CH 294178A
- Authority
- CH
- Switzerland
- Prior art keywords
- atropine
- camphorate
- preparing
- asymmetric double
- dihydrocodeinone
- Prior art date
Links
- LSPHULWDVZXLIL-UHFFFAOYSA-N (+/-)-Camphoric acid Chemical compound CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 229930003347 Atropine Natural products 0.000 claims description 10
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 claims description 10
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 claims description 10
- 229960000396 atropine Drugs 0.000 claims description 10
- LLPOLZWFYMWNKH-CMKMFDCUSA-N hydrocodone Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)CC(=O)[C@@H]1OC1=C2C3=CC=C1OC LLPOLZWFYMWNKH-CMKMFDCUSA-N 0.000 claims description 7
- 229960000240 hydrocodone Drugs 0.000 claims description 7
- LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 claims description 5
- 235000019441 ethanol Nutrition 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 208000014181 Bronchial disease Diseases 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 201000005702 Pertussis Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 208000014617 hemorrhoid Diseases 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- BULVZWIRKLYCBC-UHFFFAOYSA-N phorate Chemical compound CCOP(=S)(OCC)SCSCC BULVZWIRKLYCBC-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
Procédé de préparation d'un camphorate double asymétrique. La présente invention est relative à un procédé de préparation d'un nouveau dérivé de l'acide eamphorique, à savoir le ca.mpho- rate double asymétrique de dihydroeodéinone et d'atropine.
La dihy drocodéinone peut être représentée par la formule suivante (voir l'ouvrage lledieinal Chemistry par Alfred Burger, vol. 1, page 159)
EMI0001.0013
La préparation de camphorates acides et neutres (symétriques), tels que les campho- rates de lithium, de magnésium, (le calcium et d'ammonium, est connue.
De même, on a déjà préparé divers cam- phorates organiques acides ou neutres (symé triques), tels que ceux d'hexaméthylPne- tétrainine, d'alcaloïdes, ete.
uivant l'invention, on fait réagir succes- S <B>S</B> sivement un équivalent. moléculaire de di- hydrocodéinone et un équivalent moléculaire d'atropine sur un équivalent moléculaire d'acide camphorique. Par équivalent molécu laire, on entend ici des quantités équimolécu laires de ces trois composés. La réaction s'opère, de préfèrence, au sein d'un solvant, tel que l'alcool éthylique absolu, indifférent vis-à-vis des réactifs en présence.
Le eaniphorate de dihydrocodéinone et d'atropine se prépare avantageusement par addition successive de dihydrocodéinone dis soute clans du chloroforme et d'atropine dans une solution alcoolique d'acide camphorique. <I>Exemple:</I> On dissout 24,88 g d'acide camphorique synthétique en cristaux dans 150 ems d'alcool éthylique absolu. A la solution obtenue, on ajoute, en agitant, 39,16 g de dihydrocodéi- none base anhydre dissoute dans du chloro forme et on chauffe modérément sur plaque chauffante. Finalement, on ajoute 35,95 g d'atropine base anhydre.
Après 10 minutes de chauffage à une température n'excédant sen siblement pas 50 à 60 C, on chasse l'alcool éthylique sous vide. En laissant le résidu pâ teux au repos sous un vide de 14 mm de Hg, il prend en masse.
Le camphorate double de dihydroeodéinone et d'atropine est un produit pulvérulent, de couleur blanche, fondant vers 147 C. Il est soluble dans l'eau à. raison de 6,2 g pour 100 em3 d'eau à 20 C et dans l'alcool éthy lique à raison de 1 g pour 100 cm3 d'alcool, à 20 C, mais est insoluble dans l'éther.
En raison de la présence dans une même molécule de trois constituants possédant. une activité thérapeutique propre, on obtient des résultats avantageux en utilisant le campho- rate double de dihydrocodéinone et d'atropine, comme analgésique, dans le traitement des ca tarrhes bronchiques, des toux rebelles, de la coqueluche, des hémorroïdes, etc.
Process for preparing an asymmetric double camphorate. The present invention relates to a process for the preparation of a new derivative of eamphoric acid, namely the asymmetric double ca.phorate of dihydroeodeinone and atropine.
Dihy drocodeinone can be represented by the following formula (see the work Illieinal Chemistry by Alfred Burger, vol. 1, page 159)
EMI0001.0013
The preparation of acidic and neutral (symmetrical) camphorates, such as lithium, magnesium, (calcium and ammonium) camphorates is known.
Likewise, various acidic or neutral (symmetrical) organic camphorates have already been prepared, such as those of hexamethylPne-tetrainine, alkaloids, ete.
Following the invention, an equivalent is reacted successively. molecular weight of dihydrocodeinone and one molecular equivalent of atropine to one molecular equivalent of camphoric acid. The term “molecular equivalent” is understood here to mean equimolecular amounts of these three compounds. The reaction preferably takes place in a solvent, such as absolute ethyl alcohol, which is indifferent to the reagents present.
The dihydrocodeinone and atropine aniphorate is advantageously prepared by successive addition of dissolved dihydrocodeinone in chloroform and atropine in an alcoholic solution of camphoric acid. <I> Example: </I> 24.88 g of synthetic camphoric acid crystals are dissolved in 150 ems of absolute ethyl alcohol. To the solution obtained, 39.16 g of anhydrous dihydrocodeino-base dissolved in chloroform are added, with stirring, and the mixture is heated moderately on a hot plate. Finally, 35.95 g of anhydrous atropine base are added.
After heating for 10 minutes at a temperature not exceeding 50 to 60 ° C., ethyl alcohol is removed in vacuo. By leaving the pasty residue to stand under a vacuum of 14 mm Hg, it solidifies.
Atropine Dihydroeodeinone Double Camphorate is a powdery, white product, melting at about 147 C. It is soluble in water. an amount of 6.2 g per 100 em3 of water at 20 C and in ethyl alcohol at a rate of 1 g per 100 cm3 of alcohol, at 20 C, but is insoluble in ether.
Due to the presence in the same molecule of three constituents possessing. proper therapeutic activity, advantageous results are obtained by using the double camphorate of dihydrocodeinone and atropine, as an analgesic, in the treatment of bronchial diseases, intractable coughs, pertussis, hemorrhoids, etc.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE294178X | 1947-06-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH294178A true CH294178A (en) | 1953-10-31 |
Family
ID=3867318
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH294178D CH294178A (en) | 1947-06-17 | 1948-06-17 | Process for preparing an asymmetric double camphorate. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH294178A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE938249C (en) * | 1953-05-21 | 1956-01-26 | Knoll Ag | Process for the preparation of dihydrocodeine hydrorhodanide |
-
1948
- 1948-06-17 CH CH294178D patent/CH294178A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE938249C (en) * | 1953-05-21 | 1956-01-26 | Knoll Ag | Process for the preparation of dihydrocodeine hydrorhodanide |
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