US3149034A - Method of relieving pain with (pyridyllower alkyl)-amines - Google Patents

Method of relieving pain with (pyridyllower alkyl)-amines Download PDF

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US3149034A
US3149034A US124362A US12436261A US3149034A US 3149034 A US3149034 A US 3149034A US 124362 A US124362 A US 124362A US 12436261 A US12436261 A US 12436261A US 3149034 A US3149034 A US 3149034A
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beta
pyridyl
amines
pain
amine
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US124362A
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Jr Edgar A Ferguson
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UMIMED Inc
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom

Definitions

  • vascular headache is one of the most widely distributed headaches among civilized populations. It apparently is increased under the nervous tension of modern life and is responsible for great economic loss and personal difiiculty among those who sulfer from this disease. Most commonly the vascular headache takes the form of a migraine attack. In its first phase the attack manifests itself as an aura, dizziness, and general mental irritability and physical unrest. Medical authority states that these manifestations are precipitated by irregular and nonphysiological construction of the cerebral vessels, particularly those vessels having connection with the dura and the scalp region.
  • headache occurs alternated by severe disturbance of central origin leading to nausea, vomiting, gastrointestinal upset, and vasomotor imbalance characterized by sweating, flushing (which alternates with paling), palpitation, weakness, and general malaise.
  • These symtoms are of the same general character as the disturbance that accompanies motion sickness (seasickness) and it is postulated that they are caused by fatigue of the vessel walls causing an abnormal dilation of the cerebral vessels. It is particularly during this stage that medications give relief in accordance with their particular pharmacodynamic characteristics.
  • the abnormal dilation and contraction in the muscle of the vessel wall sometimes causes pain points to originate and thus spread impulses from these pain points to cause the flushing type of pain which is characteristically debilitating in migraine. Occasionally edema of the vessel wall will occur following a series of migraine attacks.
  • nervousness is one of the extreme accompanying symptoms which it is necessary to control and which results from the pain and strain of the migraine attacks.
  • Salicylates particularly aspirin
  • these analgesics are general pain relievers and as such raise the pain threshold of the body. In this way, it is believed, the general relief of pain is accomplished.
  • the disadvantage of dependence upon such treatment is that it does not in any way combat the physiological changes which are induced by the condition. It merely acts to relieve that pain by generally reducing the possibility of pain sensations. 'No doubt this method of treatment aids the recuperative powers of the body since the debilitating etfect of pain is somewhat overcome. There are a nurnber of other disadvantages.
  • Salicylates particularly in the form of aspirin are not always tolerated. There is the possibility of salicylate poisoning particularly in sensitive individuals.
  • the present invention provides a beta (2- or 4-pyridylalkyl)-amine most preferably in the form of beta (Z-pyridyl) ethyl methyl amine or beta (2-pyridyl) ethyl amine for the purpose of combating vascular headaches in humans.
  • the beta (2- or 4-pyridylalkyl) amine may be associated with a carrier which may be either a solid material or a sterile parenteral liquid.
  • compositions may take the form of tablets, powders, capsules, or other dosage forms which are particularly useful for oral ingestion.
  • Liquid diluents are utilized in a sterile condition for parenteral use, that is, by injection.
  • Such a medium may be a sterile solution consisting in large part of water as a solvent.
  • compositions may take the form of the active ma used in pharmaceutical manufacturing may be employed as long as there is no incompatibility with the particular beta (2- or 4-pyridylakyl) amine which is employed.
  • the particular material used may be tableted without the use of adjuvants if so desired.
  • beta (2- or 4-pyridylalkyl) amine with or without adjuvants may be placed in the usual capsule or resorptive material such as a gelatin capsule and administered in that form.
  • the beta (2- or 4-pyridylalkyl) amine composition may be put into powder packets and so usedor the composition may be prepared in the'form of a suspen sion in a substance wherein the beta" (2- or 4-pyridylalkyl) amine is not soluble.
  • the present invention embraces the use of beta (2- or 4-pyridylalkyl) amines in various forms, for example as such, or in the form'of acid addition salts of which the hydrochloride is illustrative.
  • beta (2- or 4-pyridylalkyl) amines have been found to be suitable for the purposes of the present invention.
  • the compounds should be of the following formula:
  • R2 wherein Ar is the pyridyl group attached to the radical R by its 2 or 4 carbon atom; wherein R is an ethyl, propyl or butyl group; and wherein R and R are hydrogen, methyl, ethyl, or propyl radicals. R and R may or may not be the same.
  • the most suitable compounds according to the present invention are beta (2-pyridyl) ethyl methyl amine and beta (2'-pyridyl) ethyl amine used as such or in the form of their hydrochloride addition salt. Of course the addition salt of other acids may also be used.
  • beta (2- or 4-pyridylalkyl) amines and most particularly beta (2-pyridyl) ethyl methyl amine hydrochloride and beta (Z-pyridyl) ethyl amine have particularly unobvious advantages in combating vascular headaches.
  • beta (2- or 4-pyridylalkyl) amines and acid addition salts thereof are known compounds and may be prepared by known methods (Walter, Hunt, and Fosbinder, Jour. Amer. Chem. Soc, vol. 63, p. 2771, October 1941). Insofar as is known however the physiological property of combating vascular headache has not been investigated; norhas the compound been applied for this therapeutic purpose.
  • the beta (2- or 4-pyridyl) amines and the acid addition salts thereof have been found to be particularly efficient when used to combat vascular headaches.
  • the beta (2- or 4-pyridylalkyl) amines and the acid addition salts thereof have been found to combat the symptoms of migraine and the syndrome of interim migraine most successfully.
  • the beta (2- pyridyl) ethyl methyl amine hydrochloride has been used in a dose of from 2 to 4 milligrams in man to successfully combat migraine attacks and has been used in lesser dosage to successfully increase the time interval between migraine attacks when used as an interim treatment.
  • the compounds are not only useful by oral administration but may also be effectively administered parenterally, either by subcutaneous, intramuscular, or intravenous route. Not only are these doses well tolerated with no side effects or toxic effects in human beings but much greater doses on a weight to weight basis have been given to rabbits, guinea pigs, and rats which establishes a large margin of safety between the toxic dose and the effective therapeutic dose.
  • the compounds of the present invention do not act as simple vasodilators, and in fact, simple vasodilators such as histamine are not satisfactorily effective against vascular headaches.
  • Example 1 Grams Beta (2 pyridyl) ethyl methyl amine hydrochlo- 1 ride Lactose 300
  • the above mixture is comminuted in a mixer and utilized to make 1000 #2 capsules packed so that each contains 300 milligrams of the mixture, 1 milligram each of the active ingredient.
  • Example 2 Grams The above formula is utilized after mixing with sutficient alcohol to granulate, for the purpose of manufacturing tablets, each tablet to contain 1.0 milligram of active ingredient.
  • Example 3 I Beta (2 pyridyl) ethyl methyl amine hydrochloride grams 1 Physiological salt solution cc 1000 Sterile ampules are made containing 1.1 cc. each of the above solution to permit withdrawal of 1 cc., each cc. containing 1 milligram of active ingredient.
  • Example 4 Beta (2 pyridyl) ethyl methyl amine hydrochloride grams 1 Physiological salt solution cc 1000 10.5 cc. of the above is placed in multiple dose vials, each cc. containing 1 milligram of active ingredient.
  • Example 5 Beta (2 pyridyl) ethyl methyl amine hydrochloride ..grams 0.5 Physiological salt solution cc 1000
  • Multiple dose vials are made in accordance with the above instructions each vial containing 20 cc., each cc. containing 0.5 milligram of active ingredient.
  • Example 6 Grams Beta (2 pyridyl) ethyl methyl amine hydrochloride 2 Cocoa butter 1000 Utilize the above mixture after thorough comminution to mold suppositories each suppository weighing 1 gram, containing 2 milligrams each of active ingredient.
  • compositions for combating vascular headache may take any of a variety of forms.
  • Various diluents may be employed.
  • the percentage of active ingredients in the composition may be varied. It is necessary that the active ingredient constitute a proportion such that a suitable dose may be obtained.
  • many unit dosage forms may be utilized. Although it has been found that for a 70 kilo. man less than 1 milligram per dose may be effective, the preferred embodiment of the invention is for 1 milligram unit doses. Tablets containing from 1 to 2 milligrams of active ingredient have been found to be particularly useful.
  • a preferred embodiment of the parenteral solution is manufactured in the following manner.
  • Example 7 8 liters of distilled water for injection, U.S.P., are
  • Example 8 v Grams. Beta (2-pyridyl)-ethyl methyl amine 1 Beta-lactose 300' To make 1000 capsules (No. 2) containing 1 milligram of active ingredient in each, the weight (total) of each capsule being 300 milligrams.
  • Example 9 Grams 1-(2-pyridyl)-2-methyl amino propane hydrochloride 1 Beta-lactose 300 To make No. 2 capsules, Weighing 300 milligrams each and containing 1 milligram of active ingredient each.
  • Method of treating the pains of vascular headache which comprises orally administering to a patient sufiering from the same at least one member selected from the group consisting of beta-(2-pyridyl-1ower alkyl)-arnines, beta-(4-pyridyl-lower alkyl)-amines and non-toxic acid addition salts thereof.
  • Method of relieving the pain of angina which comprises orally administering to a patient suffering from the same beta-(Z-pyridyD-ethyl methyl amine.
  • Method of relieving the pain of angina which comprises orally administering to a patient sufiering' from the same beta-(2-pyridyl)-ethyl amine.
  • Method of treating the pains of angina which comprises orally administering to a patient suffering from the same at least one member selected from the group consisting of beta-(Z-pyridyl-lower alkyl) -arnines, beta-(4- pyridyl-lower alkyl)-amines and non-toxic acid addition salts thereof.
  • Method of treating the pains of vascular headaches which comprises orally administering to a patient suffering from the same beta-(2-pyridyl)-ethyl methyl amine.
  • Method of treating the pains of vascular headaches which comprises orally administering to a patient suffering from the same beta-(2-pyridyl)-ethylamine.
  • Method of treating the pains of .Menieres syndrome which comprises orally administering to apatient sufiering from the same at least one member selected from the group consisting of beta-(2-pyridyl-lower alkyl)-amines,
  • Method of treating the pains of Raynauds disease which comprises orally administering to a patient suffering from the same at least one member selected from the group consisting of beta-(Z-pyridyl-lower aIkyD-amines, beta-(4-pyridyl-lower alkyl)-amines and non-toxic acid addition salts thereof.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

United States Patent 3,149,034- METHOD OF RELEVHNG PAIN WiTH (PYRIDYL- LUWER ALKYD-AMWES Edgar A. Ferguson, Jan, Brooklyn, N.Y., assignor, by mesne assignments, to Umimed, Erie, Morristown, N.J., a corporation of Delaware N0 Drawing. Filed .l'uly 17, 1961, Ser. No. 124,362 8 Claims. ((Jl. 167-55) This invention relates to compositions useful to combat vascular headache and in the treatment thereof. More particularly this invention relates to such compositions in which the active ingredient is a beta-(Z- or 4-pyridylalkyl)-amines or an acid addition salt thereof such as the hydrochloride or the hydroiodide.
It is known that vascular headache is one of the most widely distributed headaches among civilized populations. It apparently is increased under the nervous tension of modern life and is responsible for great economic loss and personal difiiculty among those who sulfer from this disease. Most commonly the vascular headache takes the form of a migraine attack. In its first phase the attack manifests itself as an aura, dizziness, and general mental irritability and physical unrest. Medical authority states that these manifestations are precipitated by irregular and nonphysiological construction of the cerebral vessels, particularly those vessels having connection with the dura and the scalp region. In the second stage headache occurs alternated by severe disturbance of central origin leading to nausea, vomiting, gastrointestinal upset, and vasomotor imbalance characterized by sweating, flushing (which alternates with paling), palpitation, weakness, and general malaise. These symtoms are of the same general character as the disturbance that accompanies motion sickness (seasickness) and it is postulated that they are caused by fatigue of the vessel walls causing an abnormal dilation of the cerebral vessels. It is particularly during this stage that medications give relief in accordance with their particular pharmacodynamic characteristics. The abnormal dilation and contraction in the muscle of the vessel wall sometimes causes pain points to originate and thus spread impulses from these pain points to cause the flushing type of pain which is characteristically debilitating in migraine. Occasionally edema of the vessel wall will occur following a series of migraine attacks. It is further noted that nervousness is one of the extreme accompanying symptoms which it is necessary to control and which results from the pain and strain of the migraine attacks.
Salicylates, particularly aspirin, have been used as analgesics to combat the pain of vascular headache. These analgesics are general pain relievers and as such raise the pain threshold of the body. In this way, it is believed, the general relief of pain is accomplished. The disadvantage of dependence upon such treatment is that it does not in any way combat the physiological changes which are induced by the condition. It merely acts to relieve that pain by generally reducing the possibility of pain sensations. 'No doubt this method of treatment aids the recuperative powers of the body since the debilitating etfect of pain is somewhat overcome. There are a nurnber of other disadvantages. Salicylates particularly in the form of aspirin are not always tolerated. There is the possibility of salicylate poisoning particularly in sensitive individuals. Tolerance to aspirin is developed quite commonly by individuals sufiering from vascular headache. Thus larger and larger doses maybe necessary to obtain a smaller and smaller effect. Accordingly however useful simple analgesic agents such as salicylates may be their utility is limited by these factors in addition to the fact that what relief is accomplished is not accomplished 3,149,034 Patented Sept. 15, 1964 too suffers from many disadvantages. Among the prominent disadvantages are toxicity since ergot is a specific poison. Another disadvantage is that-there are groups of patients which do not respond to ergot. Still another great disadvantage is that ergot preparations do not keep well unless special precautions are taken. These precautions include sealing in individual bottles which are airtight and protected from light. The sterile solution of ergot must also be kept out of contact with air and therefore only individual sterile ampules are used precluding the use of multiple dose vials.
Among the objects of the present invention is the production of compositions for combating not only vascular headache but also in combating a number of related conditions resulting in great sufferings to human beings,these' conditions being in general such which require a circulatory stimulant (but not a vasodilator), such as vascular headaches, angina, Menieres syndrome, and other conditions requiring increased retinal circulation.
With the above objects in view, the present invention provides a beta (2- or 4-pyridylalkyl)-amine most preferably in the form of beta (Z-pyridyl) ethyl methyl amine or beta (2-pyridyl) ethyl amine for the purpose of combating vascular headaches in humans. According to this invention the beta (2- or 4-pyridylalkyl) amine may be associated with a carrier which may be either a solid material or a sterile parenteral liquid.
The compositions may take the form of tablets, powders, capsules, or other dosage forms which are particularly useful for oral ingestion. Liquid diluents are utilized in a sterile condition for parenteral use, that is, by injection. Such a medium may be a sterile solution consisting in large part of water as a solvent.
The compositions may take the form of the active ma used in pharmaceutical manufacturing may be employed as long as there is no incompatibility with the particular beta (2- or 4-pyridylakyl) amine which is employed. The particular material used may be tableted without the use of adjuvants if so desired.
Alternatively the beta (2- or 4-pyridylalkyl) amine with or without adjuvants may be placed in the usual capsule or resorptive material such as a gelatin capsule and administered in that form. In another embodiment of the present invention the beta (2- or 4-pyridylalkyl) amine composition may be put into powder packets and so usedor the composition may be prepared in the'form of a suspen sion in a substance wherein the beta" (2- or 4-pyridylalkyl) amine is not soluble.
The present invention embraces the use of beta (2- or 4-pyridylalkyl) amines in various forms, for example as such, or in the form'of acid addition salts of which the hydrochloride is illustrative. 'All of the known beta (2- or 4-pyridylalkyl) amines have been found to be suitable for the purposes of the present invention. Most'preferably, the compounds should be of the following formula:
R2 wherein Ar is the pyridyl group attached to the radical R by its 2 or 4 carbon atom; wherein R is an ethyl, propyl or butyl group; and wherein R and R are hydrogen, methyl, ethyl, or propyl radicals. R and R may or may not be the same. The most suitable compounds according to the present invention are beta (2-pyridyl) ethyl methyl amine and beta (2'-pyridyl) ethyl amine used as such or in the form of their hydrochloride addition salt. Of course the addition salt of other acids may also be used.
It has been found that the beta (2- or 4-pyridylalkyl) amines and most particularly beta (2-pyridyl) ethyl methyl amine hydrochloride and beta (Z-pyridyl) ethyl amine have particularly unobvious advantages in combating vascular headaches. These beta (2- or 4-pyridylalkyl) amines and acid addition salts thereof are known compounds and may be prepared by known methods (Walter, Hunt, and Fosbinder, Jour. Amer. Chem. Soc, vol. 63, p. 2771, October 1941). Insofar as is known however the physiological property of combating vascular headache has not been investigated; norhas the compound been applied for this therapeutic purpose.
' The beta (2- or 4-pyridyl) amines and the acid addition salts thereof have been found to be particularly efficient when used to combat vascular headaches. In cases of migraine the beta (2- or 4-pyridylalkyl) amines and the acid addition salts thereof have been found to combat the symptoms of migraine and the syndrome of interim migraine most successfully. For example the beta (2- pyridyl) ethyl methyl amine hydrochloride has been used in a dose of from 2 to 4 milligrams in man to successfully combat migraine attacks and has been used in lesser dosage to successfully increase the time interval between migraine attacks when used as an interim treatment. As little as 0.5 milligram per day may be used as the interim treatment in vascular headaches, in order to prevent recurrence of attacks. The compounds are not only useful by oral administration but may also be effectively administered parenterally, either by subcutaneous, intramuscular, or intravenous route. Not only are these doses well tolerated with no side effects or toxic effects in human beings but much greater doses on a weight to weight basis have been given to rabbits, guinea pigs, and rats which establishes a large margin of safety between the toxic dose and the effective therapeutic dose.
It is important to note that the compounds of the present invention do not act as simple vasodilators, and in fact, simple vasodilators such as histamine are not satisfactorily effective against vascular headaches.
The following examples are given to further illustrate the present invention. The scope of the invention is not, however, meant to be limited to the specific examples.
Example 1 Grams Beta (2 pyridyl) ethyl methyl amine hydrochlo- 1 ride Lactose 300 The above mixture is comminuted in a mixer and utilized to make 1000 #2 capsules packed so that each contains 300 milligrams of the mixture, 1 milligram each of the active ingredient.
Example 2 Grams The above formula is utilized after mixing with sutficient alcohol to granulate, for the purpose of manufacturing tablets, each tablet to contain 1.0 milligram of active ingredient.
Example 3 I Beta (2 pyridyl) ethyl methyl amine hydrochloride grams 1 Physiological salt solution cc 1000 Sterile ampules are made containing 1.1 cc. each of the above solution to permit withdrawal of 1 cc., each cc. containing 1 milligram of active ingredient.
Example 4 Beta (2 pyridyl) ethyl methyl amine hydrochloride grams 1 Physiological salt solution cc 1000 10.5 cc. of the above is placed in multiple dose vials, each cc. containing 1 milligram of active ingredient.
Example 5 Beta (2 pyridyl) ethyl methyl amine hydrochloride ..grams 0.5 Physiological salt solution cc 1000 Multiple dose vials are made in accordance with the above instructions each vial containing 20 cc., each cc. containing 0.5 milligram of active ingredient.
Example 6 Grams Beta (2 pyridyl) ethyl methyl amine hydrochloride 2 Cocoa butter 1000 Utilize the above mixture after thorough comminution to mold suppositories each suppository weighing 1 gram, containing 2 milligrams each of active ingredient.
As noted above these compositions for combating vascular headache may take any of a variety of forms. Various diluents may be employed. The percentage of active ingredients in the composition may be varied. It is necessary that the active ingredient constitute a proportion such that a suitable dose may be obtained. Obviously many unit dosage forms may be utilized. Although it has been found that for a 70 kilo. man less than 1 milligram per dose may be effective, the preferred embodiment of the invention is for 1 milligram unit doses. Tablets containing from 1 to 2 milligrams of active ingredient have been found to be particularly useful.
A preferred embodiment of the parenteral solution is manufactured in the following manner.
Example 7 8 liters of distilled water for injection, U.S.P., are
filled into a 20 liter Pyrex glass bottle. To this 10 grams of beta-(2 pyridyl)-ethyl methyl amine hydrochloride are added with stirring until solution is effected. The pH is adjusted with suffiicent reagent grade normal tenth HCl to which has been added 0.03 gram per 1000 of monosodiumphosphate to achieve a pH of approximately 6.0. Then sufficient water for injection is added to bring the volume to 10 liters. The solution is filled into clean, dry, sterile, flint glass ampules, each containing 2.2 cc. of the fluid. The ampules are sealed and sterilized for a period of 30 minutes at F.
Example 8 v Grams. Beta (2-pyridyl)-ethyl methyl amine 1 Beta-lactose 300' To make 1000 capsules (No. 2) containing 1 milligram of active ingredient in each, the weight (total) of each capsule being 300 milligrams.
Example 9 Grams 1-(2-pyridyl)-2-methyl amino propane hydrochloride 1 Beta-lactose 300 To make No. 2 capsules, Weighing 300 milligrams each and containing 1 milligram of active ingredient each.
Example Grams Beta-(2-pyridyl)-ethyl amine hydrochloride 1 Beta-lactose 300 To make No. 2 capsules, weighing 300 milligrams each and containing 1 milligram of active ingredient each.
Without further analysis, the foregoing will so fully reveal the gist of the present invention that others can by applying current knowledge readily adapt it for various applications Without omitting features that, from the standpoint of prior art, fairly constitute essential characteristics of the generic or specific aspects of this invention and, therefore, such adaptations should and are intended to be comprehended Within the meaning and range of equivalence of the following claims.
What is claimed as new and desired to be secured by Letters Patent is:
1. Method of treating the pains of vascular headache, which comprises orally administering to a patient sufiering from the same at least one member selected from the group consisting of beta-(2-pyridyl-1ower alkyl)-arnines, beta-(4-pyridyl-lower alkyl)-amines and non-toxic acid addition salts thereof.
2. Method of relieving the pain of angina, which comprises orally administering to a patient suffering from the same beta-(Z-pyridyD-ethyl methyl amine.
3. Method of relieving the pain of angina which comprises orally administering to a patient sufiering' from the same beta-(2-pyridyl)-ethyl amine.
4. Method of treating the pains of angina, Which comprises orally administering to a patient suffering from the same at least one member selected from the group consisting of beta-(Z-pyridyl-lower alkyl) -arnines, beta-(4- pyridyl-lower alkyl)-amines and non-toxic acid addition salts thereof.
5. Method of treating the pains of vascular headaches, Which comprises orally administering to a patient suffering from the same beta-(2-pyridyl)-ethyl methyl amine.
6. Method of treating the pains of vascular headaches, which comprises orally administering to a patient suffering from the same beta-(2-pyridyl)-ethylamine.
7. Method of treating the pains of .Menieres syndrome which comprises orally administering to apatient sufiering from the same at least one member selected from the group consisting of beta-(2-pyridyl-lower alkyl)-amines,
beta-(4-pyridyl-lower alkyl)-aniines and non-toxic acid addition salts thereof.
8. Method of treating the pains of Raynauds disease, which comprises orally administering to a patient suffering from the same at least one member selected from the group consisting of beta-(Z-pyridyl-lower aIkyD-amines, beta-(4-pyridyl-lower alkyl)-amines and non-toxic acid addition salts thereof.
References Cited in the file of this patent

Claims (1)

1. METHOD OF TREATING THE PAINS OF VASCULAR HEADACHE, WHICH COMPRISES ORALLY ADMINISTERING TO A PATIENT SUFFERING FROM THE SAME AT LEAST ONE MEMBER SELECTED FROM THE GROUP CONSISTING OF BETA-(2-PYRIDYL-LOWER ALKYL)-AMINES, BETA-(4-PYRIDYL-LOWER ALKYL)-AMINES AND NON-TOXIC ACID ADDITION SALTS THEREOF.
US124362A 1961-07-17 1961-07-17 Method of relieving pain with (pyridyllower alkyl)-amines Expired - Lifetime US3149034A (en)

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US124362A US3149034A (en) 1961-07-17 1961-07-17 Method of relieving pain with (pyridyllower alkyl)-amines
GB26725/62A GB945095A (en) 1961-07-17 1962-07-11 Preparation for the treatment of vascular headache
FR904234A FR2338M (en) 1961-07-17 1962-07-17 New remedies intended in particular for the treatment of headaches of vascular origin.

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4165376A (en) * 1971-01-29 1979-08-21 Lake Shore Roentgenology, Ltd. Treatment of the acute after-effects resulting from alcohol ingestion
RU2356539C2 (en) * 2006-12-28 2009-05-27 Закрытое Акционерное Общество "Канонфарма Продакшн" Solid formulation betahistine dihydrochloride and related production procedure

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE464275B (en) * 1989-07-31 1991-04-08 Aagerup Bengt NEW USE OF BETA-RECEPTOR BLOCKER FOR PREPARING A PREPARATION FOR MENIER'S DISEASE
BRPI0912126A2 (en) 2008-05-27 2015-11-03 Univ Melbourne method of treating mammals with eustachian tube dysfunction

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4165376A (en) * 1971-01-29 1979-08-21 Lake Shore Roentgenology, Ltd. Treatment of the acute after-effects resulting from alcohol ingestion
RU2356539C2 (en) * 2006-12-28 2009-05-27 Закрытое Акционерное Общество "Канонфарма Продакшн" Solid formulation betahistine dihydrochloride and related production procedure

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GB945095A (en) 1963-12-23

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