US1861543A - Ephedrine salts and oil solutions thereof - Google Patents
Ephedrine salts and oil solutions thereof Download PDFInfo
- Publication number
- US1861543A US1861543A US440152A US44015230A US1861543A US 1861543 A US1861543 A US 1861543A US 440152 A US440152 A US 440152A US 44015230 A US44015230 A US 44015230A US 1861543 A US1861543 A US 1861543A
- Authority
- US
- United States
- Prior art keywords
- ephedrine
- salts
- combined
- fatty acid
- salt
- 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.)
- Expired - Lifetime
Links
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical class CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 title description 56
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 17
- 229960002179 ephedrine Drugs 0.000 description 17
- 235000014113 dietary fatty acids Nutrition 0.000 description 10
- 239000000194 fatty acid Substances 0.000 description 10
- 229930195729 fatty acid Natural products 0.000 description 10
- 150000004665 fatty acids Chemical class 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 239000002480 mineral oil Substances 0.000 description 7
- 235000010446 mineral oil Nutrition 0.000 description 7
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 5
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 5
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 101150065749 Churc1 gene Proteins 0.000 description 3
- 239000004264 Petrolatum Substances 0.000 description 3
- 229930013930 alkaloid Natural products 0.000 description 3
- 150000003797 alkaloid derivatives Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000003925 fat Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229940066842 petrolatum Drugs 0.000 description 3
- 235000019271 petrolatum Nutrition 0.000 description 3
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 3
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 3
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 2
- 102100038239 Protein Churchill Human genes 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 2
- 229960003656 ricinoleic acid Drugs 0.000 description 2
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 2
- 230000035807 sensation Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
- C07C215/28—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
- C07C215/30—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings containing hydroxy groups and carbon atoms of six-membered aromatic rings bound to the same carbon atom of the carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/138—Aryloxyalkylamines, e.g. propranolol, tamoxifen, phenoxybenzamine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
Definitions
- Ephedrine has been found of decided benefit in the treatment of certain respiratory affections as of the nose, throat and associated organs. ⁇ Vhen used in such treatment there is an initial stin which creates an unpleasant sensation and renders the use of the same objectionable to some patients.
- One method of producing a salt of this character is by combining ephedrine with a fatty acid having not less than nine carbon atoms.
- the method of preparation may consist of intimately mixin in molecular proportions the ephedrine and preferably an unsaturated fatty acid having preferably not less than nine carbon atoms. In those cases where the fatty acid is solid at room temperature it is melted before the ephedrine is stirred in.
- the resultant compound is also soluble in water giving a soapy solution or a collodial suspension.
- Various fatty acids may be used and combined with the ephedrineto produce the ephedrine salts and any of the resultant salts may be combined or mixed with mineral or other oils or fats and will be heldin solution therein, although so far as we have been able to determine at resent we have found that combining ephe rine with oleic acid or with erucic acid produces an ephedrine salt which is more readily soluble in mineral oil.
- canomomcncm ca nnflooownnnc a- Cs acH(0 )CHCHa CH;NH OOC(CHalxeCHacnncrnon)once cmnmoocwnghcmc mcmomcncm cammoocwamcm.
- An ephedrine salt consisting of ephedrine combined with a fatty acid having more than eight carbon atoms.
- An ephedrine salt consisting of ephedrine combined with an unsaturated fatty acid having more than eight carbon atoms.
- An ephedrine salt consisting of ephedrine combined with erucic acid.
- An ephedrine salt consisting of cpl drine combined with erucic acid.
- An ephedrine salt consisting of eph drine combined with ricinoleic acid.
- the compounds formed by the union of ephedrine with unsaturated fatt acids are more soluble in mineral oil, such or instance as light liquid petrolatum and have less tendency to form solid solution, although we have found that even the compounds formed by the union of ephedrine with saturated fatty acid Where the fatty acids have not less than nine carbon atoms are quite soluble in oil and fats.
- An ephedrine salt consisting of ephedrine combined with a fatty acid having more than eight carbon atoms.
- An ephedrine salt consisting of ephedrine combined with an unsaturated fatty acid having more than eight carbon atoms.
- An ephedrine salt consisting of ephedrine combined with erucic acid.
- An ephedrine salt consisting of cpl drine combined with erucic acid.
- An ephedrine salt consisting of eph drine combined with ricinoleic acid.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Paper (AREA)
- Detergent Compositions (AREA)
Description
Patented June 7, 1932 UNITED STATES PATENT OFFICE EDMOND E. MOORE AND EDGAR B. CARTER, OF INDIANAPOLIS, INDIANA, ASSIGNOBS, BY MESNE ASSIGNMENTS, TO ABBOTT LABORATORIES, OF CHICAGO, ILLINOIS, A
CORPORATION OF ILLINOIS EPHEDRINE SALTS AND OIL SOLUTIONS THEREOF Ho Drawing.
It is the purpose of our invention to produce an ephedrine salt, and it is a further object of our invention to produce an ephedrine salt which shall be soluble in oil, preferably mineral oil (liquid petrolatum).
Ephedrine has been found of decided benefit in the treatment of certain respiratory affections as of the nose, throat and associated organs. \Vhen used in such treatment there is an initial stin which creates an unpleasant sensation and renders the use of the same objectionable to some patients.
We have discovered that this sting is due to the fact that the ephedrine is a strongly basic alkaloid.
We have discovered that when the alkaloid ephedrine is combined with a fatty acid it produces a salt which, when used, does not cause the stinging sensation produced by the alkaline nature of the alkaloid ephedrine, and this salt is soluble in mineral oil. While we have specifically stated that one of the objects is to provide an ephedrine derivative which is soluble in mineral oil it will be understood that the product is also soluble in other oils and in fats, and furthermore it will be understood that while we produce a salt, which is particularly useful because of its solubility in oil and because of its nonstinging nature such salt has other uses and other applications. One method of producing a salt of this character is by combining ephedrine with a fatty acid having not less than nine carbon atoms. The method of preparation may consist of intimately mixin in molecular proportions the ephedrine and preferably an unsaturated fatty acid having preferably not less than nine carbon atoms. In those cases where the fatty acid is solid at room temperature it is melted before the ephedrine is stirred in.
The resultant compound is also soluble in water giving a soapy solution or a collodial suspension. The ephedrine salts or soaps above produced greatly lower the surface tension so that the resultant solution tends to form foam and bubbles when agitated. These salts are quite useful as emulsifying agents The ephedrine salts thus produced, that is the ephedrine salts produced by the com- Applicatlon filed March 28, 1930. Serial No. 440,152.
hinin of ephedrine with a fatty acid of not less t an nine carbon atoms is soluble in mineral oil (liquid petrolatum) and the solubility of these salts in mineral oil increases with the number of carbon atoms in the acid from which the ephedrine salt is made, even though the solution of the salts formed with the fatty acids having the higher carbon content becomes solid at room temperatures.
Various fatty acids may be used and combined with the ephedrineto produce the ephedrine salts and any of the resultant salts may be combined or mixed with mineral or other oils or fats and will be heldin solution therein, although so far as we have been able to determine at resent we have found that combining ephe rine with oleic acid or with erucic acid produces an ephedrine salt which is more readily soluble in mineral oil.
However, the following are formulas of ephedrine salts which are quite satisfactory.
muses (on CHCHa cnmmoocwnn cm.
comcmomcacm ona moocwnnwom.
qmcammcncn,
CHIN I )HCHI.
canomomcncm ca nnflooownnnc a- Cs acH(0 )CHCHa CH;NH OOC(CHalxeCHacnncrnon)once cmnmoocwnghcmc mcmomcncm cammoocwamcm.
omscmomcncna CHaNHgOGC CH2) u a mmcmomcncn CHaNHgOOC(CH2l1s H- (amen omcncna CH N H OOC (C a)1sC a- CGH5CH(OH)CHCH:|
on, n,ooo(cnfl).ion=en,.
canon 01; cHcH,
CH NHgOOC (CH2)1 CHCH.CH( OH) (C :)s a- The compounds formed by the union of ephedrine with unsaturated fatt acids are more soluble in mineral oil, such or instance as light liquid petrolatum and have less tendency to form solid solution, although we have found that even the compounds formed by the union of ephedrine with saturated fatty acid Where the fatty acids have not less than nine carbon atoms are quite soluble in oil and fats.
We have also found that one molecular equivalent of ephedrine combines with exactly one molecular equivalent of fatty acid.
We claim the following:
1. An ephedrine salt consisting of ephedrine combined with a fatty acid having more than eight carbon atoms.
2. An ephedrine salt consisting of ephedrine combined with an unsaturated fatty acid having more than eight carbon atoms.
3. An ephedrine salt consisting of ephedrine combined with erucic acid.
4. An ephedrine salt consisting of cpl drine combined with erucic acid.
5. An ephedrine salt consisting of eph drine combined with ricinoleic acid.
In witness whereof, we have hereunto set our hands at Indianapolis, Indiana, this 27th day of March, A. I). one thousand nine hundred and thirty.
EDMOND E. MOORE. EDGAR B. CARTER.
CERTIFICATE OF CORRECTION.
Patent No. 1,861,543. June 7, 1932.
EDMOND E. MOORE, ET AL.
It is hereby certified that error appears in the printed specification of the above numbered patent requiring correction as follows: Page 2, line 24, claim 4, for "erucic" read oleic; and that the said Letters Patent should be read with this correction therein that the same may onform to the record of the case in the Patent Office.
Signed and sealed this 30th day of January, A. D. 1934.
F. M. Hopkins (Seal) Acting Commissioner of Patents.
The compounds formed by the union of ephedrine with unsaturated fatt acids are more soluble in mineral oil, such or instance as light liquid petrolatum and have less tendency to form solid solution, although we have found that even the compounds formed by the union of ephedrine with saturated fatty acid Where the fatty acids have not less than nine carbon atoms are quite soluble in oil and fats.
We have also found that one molecular equivalent of ephedrine combines with exactly one molecular equivalent of fatty acid.
We claim the following:
1. An ephedrine salt consisting of ephedrine combined with a fatty acid having more than eight carbon atoms.
2. An ephedrine salt consisting of ephedrine combined with an unsaturated fatty acid having more than eight carbon atoms.
3. An ephedrine salt consisting of ephedrine combined with erucic acid.
4. An ephedrine salt consisting of cpl drine combined with erucic acid.
5. An ephedrine salt consisting of eph drine combined with ricinoleic acid.
In witness whereof, we have hereunto set our hands at Indianapolis, Indiana, this 27th day of March, A. I). one thousand nine hundred and thirty.
EDMOND E. MOORE. EDGAR B. CARTER.
CERTIFICATE OF CORRECTION.
Patent No. 1,861,543. June 7, 1932.
EDMOND E. MOORE, ET AL.
It is hereby certified that error appears in the printed specification of the above numbered patent requiring correction as follows: Page 2, line 24, claim 4, for "erucic" read oleic; and that the said Letters Patent should be read with this correction therein that the same may onform to the record of the case in the Patent Office.
Signed and sealed this 30th day of January, A. D. 1934.
F. M. Hopkins (Seal) Acting Commissioner of Patents.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US440152A US1861543A (en) | 1930-03-29 | 1930-03-29 | Ephedrine salts and oil solutions thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US440152A US1861543A (en) | 1930-03-29 | 1930-03-29 | Ephedrine salts and oil solutions thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1861543A true US1861543A (en) | 1932-06-07 |
Family
ID=23747652
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US440152A Expired - Lifetime US1861543A (en) | 1930-03-29 | 1930-03-29 | Ephedrine salts and oil solutions thereof |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1861543A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2437504A (en) * | 1948-03-09 | Thiamin dioctylsulfosuccjinate | ||
| US3304230A (en) * | 1963-02-18 | 1967-02-14 | Revlon | Liquid aerosol propellant solutions of fatty acid salts of physiologically active amines |
| US4663474A (en) * | 1983-02-22 | 1987-05-05 | Pfizer Inc. | Synthetic intermediates for a chiral 3-(substituted-phenyl)-4-(3-hydroxypropyl) cyclohexanol |
-
1930
- 1930-03-29 US US440152A patent/US1861543A/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2437504A (en) * | 1948-03-09 | Thiamin dioctylsulfosuccjinate | ||
| US3304230A (en) * | 1963-02-18 | 1967-02-14 | Revlon | Liquid aerosol propellant solutions of fatty acid salts of physiologically active amines |
| US4663474A (en) * | 1983-02-22 | 1987-05-05 | Pfizer Inc. | Synthetic intermediates for a chiral 3-(substituted-phenyl)-4-(3-hydroxypropyl) cyclohexanol |
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