US2991225A - Omicron-methylbenzhydryl-beta-dimethylaminoethyl ether process and composition for symptomatic relief of the syndrome of parkinsonism and of spastic skeletal muscle disorders - Google Patents
Omicron-methylbenzhydryl-beta-dimethylaminoethyl ether process and composition for symptomatic relief of the syndrome of parkinsonism and of spastic skeletal muscle disorders Download PDFInfo
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- US2991225A US2991225A US647756A US64775657A US2991225A US 2991225 A US2991225 A US 2991225A US 647756 A US647756 A US 647756A US 64775657 A US64775657 A US 64775657A US 2991225 A US2991225 A US 2991225A
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- skeletal muscle
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- methylbenzhydryl
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- 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
Description
United States Patent The invention relates to a process for the treatment of Parkinsonism, obsession, depression and skeletal muscle disorders, and medicines to be used for this purpose. The application is a continuation in part of my copending application Serial No. 580,686, filed April 25, 1956 (now abandoned), as a continuation in part of my application No. 345,837, filed March 31, 1953 (now abandoned).
fi-Dimethylaminoethyl benzhydrylether (diphenhydramine) is a well know anti-histaminic. It is also an effective medicine against travel sicknesses.
According to Leonard et a1. (National Research Counsel Chemical Biological Coordination Centre Review, No. 3, 1950, pages 76-79, 84 and 112-422), Rieveschl c.s., mentioned a number of corresponding amino ethers in which one or both phenyl nuclei contain substituents, i.a. the ortho-methyl compound, with regard to their antihistaminic properties. They have found, however, that the anti-histaminic action of the last mentioned compound is inferior to that of the unsubstituted compound and since obviously the unsubstituted compound is easier to prepare and less expensive there would be no advantage in using the orthomethyl compounds as an anti-histaminic.
I have now found that said orthomethyl compound is a powerful medicine against Parkinsonism, obsession, depression and skeletal muscle disorders and the invention therefore has for its object a process for the treatment of Parkinsonism, obsession, depression and skeletal muscle disorders which comprises administering 50 to 300 milligrams per day of a member of the class consisting of fl-dimethylaminoethyl o-methyl benzhydryl ether, and its salts to humans suffering from Parkinsonism, obsession and depression. Y
Parkinsons disease is very often complicated by suc disturbing symptoms as akinesia, weakness, tiredness and mental depression. To some extent these accompanying symptoms are cured by current remedies such as Amphetamine, Arthane, Pagitane and Kemadrine.
However, much isleft to be desired in terms of relief of many sufferers from Parkinsons disease. Moreover some patients who use the above mentioned remedies cannot be treated with analeptics, because of the aggravation of tremor.
I have found that the above mentioned orthomethyl compound and its salts are exceptionally beneficial in curing the above mentioned and other frequently occurring accompanying side-effects of Parkinsonism.
Obsession and depression in other cases than those in which they are caused by Parkinsonism until some years ago could only be treated by shock therapy and psychiatric care. More recently several therapeutics described as ataraxic drugs or tranquilizers have been introduced in 'ice For instance, the side-effects of chlorpromazine, one of these drugs, include dryness of the mouth, nasal congestion, constipation, skin rash, dizziness, postural hypoten sion, jaundice and even agranulo-cytosis.
Reserpine, another veryfrequently prescribed drug for; the treatment of patients suifering from mental diseases, shows i.a. the following side-efiects:
Parkinson-like symptoms, such as tremors and excessive salivation. V
Inertia, sleepiness, drowsiness, feelings of fatigue, generalised flushing.
Cardiovascular eifects cardia. I
Miosis, confusion, paresthesiae, mild gastro-intestinal disturbances.
Nasal stufliness, infection of the conjunctivae and nasal mucous membrane.
I have found that fi-dimethylaminoethyl orthomethylbenzhydrylether and its salts, when administered to humans suifering from obsession and depression, also exhibit very beneficial effects without any indication of disturbing side'effects.
For curing skeletal muscle disorders, besides physical therapy, in serious cases muscle relaxants have been used. Said relaxants were divided into two main groups, viz. those acting on, or in the vicinity of, myoneural juncture and those aifecting the basal ganglia and the reflex of excitability of nerve centres.
The first group consisted of naturally occurring curare alkaloids and curare-like drugs. As an example of the second group of relaxants Mephenesin (3-orthotoloxy- 1,2-propanediol) can be mentioned. However, it has appeared that this division into two groups was not justified because more recent evidence showed that several, possibly most of the agents that paralyse the neuromuscular end plate also interfere seriously with the circulation by block of ganglia. The entire group of drugs has its chief usefulness in the production of relaxation during surgical anesthesia. The skeletal muscle relaxants however, may cause serious side-eifects such as respiratory failure and circulatory collapse even when administered in dosages not exceeding those usually well toleratedby most patients. Up till now these circulatory collapses could not be satisfactorily controlled.
Although the oral use of Mephenesin does not seem to be accompanied by serious side-effects there are some disadvantages which strongly restrict the usefulness of this drug, viz. that very large dosages amounting to 1 to 3 grams have to be administered daily and that often only a temporary relief is obtained.
I have now found that B-dimethylaminoethyl orthomethylbenzhydrylether and its salts, when administered to humans suffering from skeletal muscle disorders exhibit very definitely beneficial elfects, and that said beneficial effects are not of a temporary character but long lasting.
From the skeletal muscle disorders which can be treated with excellent results may be mentioned: Acute tOI", ticollis, severe leg muscle spasm, myositis, fibrositis, lumbosacral herniated disc, rheumatoid spondylitisand post-menopausal osteoporosis. This enumerationis fnot such as hypotension and bradyto be regarded as limitative. In none of the above. men:
tioned examples of skeletal muscle disorders-treated with the ortho-methyl compound or one of its salts thetreat ment was complicated by the-occurrenceofmnwanted side-effects. In quite a few instancesithepatients" I151. sponded excellently within ten days of treatment.
Patented July 4, 1961 These new tranquilizing drugs have The invention therefore has for its general object a process for the treatment of an illness of the group consisting of Parkinsonism, obsession, depression and skeletal muscle disorders which comprises administering 50 to 300 milligrams per day of a member of the class consisting of fi-dimethylaminoethyl o-methylbenzhydryl ether and its salts to humans suflfering from Parkinsonism, obsession and depression.
The invention also has for its object a medicine against an illness of the group consisting of Parkinsonism, obsession, depression and skeletal muscle disorders comprising a member of the class consisting of fi-dimethylamino ethyl o-methylbenzhydryl ether and its salts in admixture with a solid carrier or diluent.
It has appeared that B-dimethylamino ethyl o-methylbenzhydrylether and its salts are not only very efiective in combating Parkinsonism, obsession, depression and skeletal muscle disorders but that at the same time they have a low toxicity which is even somewhat lower than that of the unsubstituted compound.
Suitable diluents are e.g. corn starch, oxidized potato starch, lactose, stearic (acid also in the form of the magnesium salt), talcum, heavy magnesium oxide, magnesium carbonate, certain diatomaceous earths, waxes, gums and sugars.
Said medicines are preferably administered by the oral way, e.g. in the form of powders or in moulded form, such as tablets. It is also possible however to use solutions of the substances for injection purposes, preferably for parenteral injections, e.g. in the case of obsession and depression.
The o-methyl compound referred to above also has a certain local-anesthetic action. To some extent this is a drawback as the medicines will cause a disagreeable sensation at the places of the mouth with which the substance comes into contact. This drawback can be obviated by administering the compound in such a form that during the time which it takes the preparation to pass the mouth and the pharynx the active substance will not yet be dissolved but that it will decompose with suflicient rapidity in the gastric juice. This end can be attained, for example, in the following way:
(a) The active component, previously mixed with the usual constituents of the tablet, e.g. starch, magnesium stearate, tallow and the like, is coated with an aqueous solution of a cellulose ester, carboxymethyl cellulose, collagen, gelatin, sodium alginate, plant slime, pectin, agar-agar or the like.
(b) The active component is coated with a fat which is liquid at body temperature, so as to produce a coating which gives a sufficient protection in the mouth, but which will dissolve in the stomach and enable the active component to be dissolved in the gastric juice.
(c) The active component is incorporated into a tablet in the conventional manner and this tablet is provided with a very thin sugar coating.
The active substance is preferably used in the form of a salt, e.g. the hydrochloric acid salt. Other salts, e.g. the oxalic acid salt, however, may also be used.
The invention will be illustrated by the following examples:
Example I A mixture of the following composition is prepared:
50 g. o-methylbenzhydryl-[i-dimethylaminoethyl ether hydrochloride 50 g. lactose 40 g. oxidized starch 5 g. talcum 5 g. magnesium stearate This mixture is made into tablets oi 150 mg. If desued the tablet may be provided with a coating.
4 Example 2 A mixture of the following composition is prepared:
50 g. o-methylbenzhydryl-p-dimethylaminoethyl ether hydrochloride 50 g. lactose 25 g. corn starch 10 g. talcum 5 g. stearic acid The mixture is made into tablets of 140 mg. which are subsequently provided with a sugar coating, the weight of said coating being about 35 mg. per tablet.
I claim:
1. A process for the symptomatic relief of the syndrome of Parkinsonism, including obsession, depression, and skeletal muscle disorders, which comprises administering 50 to 300 milligrams per day of a member of the class consisting of fi-dimethylamino-ethyl o-methylbenzhydryl ether and its salts to humans displaying the symptoms of said syndrome.
' 2. Process for the treatment of humans sufiering from depression which comprises administering 50 to 300 milligrams per day of a salt of fi-dimethylaminoethyl omethylbenzhydryl ether to a human suffering from depression.
3. Process for the treatment of humans sulfering from depression which comprises administering 50 to 300 milligrams per day of fi-dimethylaminoethyl o-methylbenzhydryl ether hydrochloride to a human sufien'ng from depression.
4. Process for the treatment of humans sufiering from spastic skeletal muscle disorders which comprises administering 50 to 300 milligrams per day of a salt of fi-dimethylaminoethyl o-methylbenzhydryl ether to a human sufiering from such spastic skeletal muscle disorder.
5. Process for the treatment of humans suffering from spastic skeletal muscle disorders which comprises administering 50 to 300 milligrams per day of B-dimethylaminoethyl o-methylbenzhydryl 'ether hydrochloride to a human suffering from such spastic skeletal muscle disorder.
6. Medicine eflective for the symptomatic relief of the syndrome of Parkinsonism, including obsession, depression, and skeletal muscle disorders, said medicine comprising as the active component a member of the class consisting of fi-dimethylaminoethyl o-methylbenzhydryl ether and its salts, and a solid carrier, and a substance covering at least said active component effective to prevent release of said active component in the mouth and to provide release in the stomach, said substance being a member of the group consisting of a cellulose ester, carboxymethyl cellulose, collagen, gelatin, sodium alginate, plant slime, pectin, and agar-agar.
7. A composition in dosage unit form for the symptomatic relief of the syndrome of Parkinsonism, including obsession, depression, and skeletal muscle disorders, comprising as the active component not less than 10 mg. of a member selected from the group consisting of fl-dimethylaminoethyl o-methylbenzhydryl ether and its salts per dosage unit, and a solid pharmaceutical carrier, and a substance covering at least said active component efl'ective to prevent release of said active component in the mouth and to provide release in the stomach, said substance being a member of the group consisting of a cellulose ester, carboxymethyl cellulose, collagen, gelatin, sodium alginate, plant slime, pectin, and agar-agar.
8. A composition in dosage unit form for the symptomatic relief of the syndrome of Parkinsonism, including obsession, depression, and skeletal muscle disorders, comprising as the active component about 10 to about mg. of p-dimethylaminoethyl o-methylbenzhydryl ether hydrochloride per dosage unit, and a solid pharmaceutical carrier, and a substance covering at least said active. component effective to prevent release of said. active component in the mouth and to provide release in the stomach, said substance being a member of the group consisting of a cellulose ester, carboxymethyl cellulose, collagen, gelatin, sodium alginate, plant slime, pectin, and agar-agar.
9. A composition in dosage unit form for the symptomatic relief of the syndrome of Parkinsonism, including obsession, depression, and skeletal muscle disorders, comprising as the active component about to about 100 mg. of a member of the class consisting of B-dimethylaminoethyl o-methylbenzhydryl ether and its salts, and a solid pharmaceutical carrier, and a substance covering at least said active component effective to prevent release of said active component in the mouth and to provide release in the stomach, said substance being a member of the group consisting of a cellulose ester, carboxymethyl cellulose, collagen, gelatin, sodium alginate, plant slime, pectin, and agar-agar.
10. Medicine effective for the symptomatic relief of the syndrome of Parkinsonism, including obsession, depression, and skeletal muscle disorders, said medicine comprising as the active component a member of the class consisting of fi-dimethylaminoethyl o-methylbenzhydryl ether and its salts, and a fat which is liquid at body temperature covering said active component eifective to prevent release of said active component in the mouth and to provide release in the stomach.
11. A composition in dosage unit form for the symptomatic relief of the syndrome of Parkinsonism, including obsession, depression, and skeletal muscle disorders, comprising as the active component not less than 10 mg. of a. member selected from the group consisting of fl-dimethylaminoethyl o-methylbenzhydryl ether and its salts per dosage unit and a fat which is liquid at body temperature covering said active component effective to prevent release of said active component in the mouth and to provide release in the stomach.
12. A composition in dosage unit form for the symptomatic relief of the syndrome of Parkinsonism, including obsession, depression, and skeletal muscle disorders, comprising as the active component about 10 to about 100 mg. of p-dimethylaminoethyl o-methylbenzhydryl ether hydrochloride and a fat which is liquid at body temperature covering said active component effective to prevent release of said active component in the mouth and to provide release in the stomach.
13. A composition in dosage unit form for the symptomatic relief of the syndrome of Parkinsonism, including obsession, depression, and skeletal muscle disorders, comprising as the active component about 10 to about 100 mg. of a member selected from the group consisting of p-dimethylaminoethyl o-methylbenzhydryl ether and its salts per dosage and a fat which is liquid at body temperature covering said active component effective to prevent release of said active component in the mouth and to provide release in the stomach.
14. Medicine eifective for the symptomatic relief of the syndrome of Parkinsonism, including obsession, depression, and skeletal muscle disorders, said medicine comprising as the active component a member of the class consisting of p-dimethylaminoethyl o-methylbenzhydryl ether and its salts tableted with a solid carrier, the tablet being provided with a very thin sugar coating efiective to prevent release of said active component in the mouth and to provide release in the stomach.
15. A composition in dosage unit form for the symptomatic relief of the syndrome of Parkinsonism, including obsession, depression, and skeletal muscle disorders, comprising as the active component not less than 10 mg. of a member selected from the group consisting of fl-dimethylaminoethyl o-methylbenzhydryl ether and its salts per dosage unit tableted with a solid pharmaceutical carrier, the tablet being provided with a very thin sugar coating effective to prevent release of said active component in the mouth and to provide release in the stomach.
16. A composition in dosage unit form for the symptomatic relief of the syndrome of Parkinsonism, including obsession, depression, and skeletal muscle disorders, com prising as the active component about 10 to about mg. of fl-dimethylaminoethyl o-methylbenzhydryl ether hydrochloride tableted with a solid pharmaceutical carrier, the tablet being provided with a very thin sugar coating eifective to prevent release of said active component in the mouth and to provide release in the stomach.
17. A composition in dosage unit form for the symptomatic relief of the syndrome of Parkinsonism, including obsession, depression, and skeletal muscle disorders, comprising as the active component about 10 to about 100 mg. of a member of the class consisting of p-dimethylaminoethyl o-methylbenzhydryl ether and its salts per dosage unit tableted with a solid pharmaceutical carrier, the tablet being provided with a very thin sugar coating efiective to prevent release of said active component in the mouth and to provide release in the stomach.
References Cited in the file of this patent f UNITED STATES PATENTS 2,397,799 Martin et a1. Apr. 2, 1946 2,421,714 Rieveschl June 3, 1947 2,453,729 Rieveschl Nov. 16, 1948 2,454,092 Rieveschl Nov. 16, 1948 2,479,843 Knox et a1. Aug. 23, 1949 2,483,434 Rieveschl Oct. 4, 1949 2,483,436 Rieveschl Oct. 4, 1949 2,483,671 Rieveschl Oct. 4, 1949 2,508,422 Rieveschl May 23, .1950 2,534,813 Cusic Dec. 19, 1950 2,567,350 Rieveschl Sept. 11, 1951 2,567,351 Rieveschl Sept. 11, 1951 2,577,234 Cusic Dec. 4, 1951 2,598,530 Gakenheimer May 27, 1952 FOREIQLN PATENTS 285,091 Great Britain June 10, 1929 638,606 Great Britain June 14, 1950 OTHER REFERENCES Ghinn: Squibb Abstract Bull, vol. 24, No. 8, Feb. 21, 1951, page A151.
Leonard et al.: National Research Council Chemical Biological Coordination Center Review, No. 3, Histamine Antagonists, 1950, pages 76-79, 84, 112-122.
5Merck Index (7th ed., 1960), Orphenadrine, page 7 8.
Disipal Colloquium, Amersfoort, March 21, 1959, 72 p., published by Brocades-Stheeman 8: Pharmacia.
Loew: Physiological Reviews, vol. 27, No. 4, October 1947, page 542.
Goodman and Gilman: Pharmacological Basis of Therapeutics, 2nd ed., The MacMillan Company, 1955, page 555.
Churchill et al.: I.A.M.A., vol. 141, No. 1, pp. 18-21, Sept. 3, 1949.
Pettit: Amer. Practitioner, pp. 662-3, July 1949.
Claims (1)
1. A PROCESS FOR THE SYMPTOMATIC RELIEF OF THE SYNDROME OF PARKINSONISM, INCLUDING OBSESSION, DEPRESSION, AND SKELETAL MUSCLE DISORDERS, WHICH COMPRISES ADMINISTERING 50 TO 300 MILLIGRAMS PER DAY OF A MEMBER OF THE CLASS CONSISTING OF B-DIMETHYLAMINO-ETHYL O-METHYLBENZHYDRYL ETHER AND ITS SALTS TO HUMANS DISPLAYING THE SYMPTOMS OF SAID SYNDROME.
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NL2991225X | 1952-04-08 |
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US647756A Expired - Lifetime US2991225A (en) | 1952-04-08 | 1957-03-22 | Omicron-methylbenzhydryl-beta-dimethylaminoethyl ether process and composition for symptomatic relief of the syndrome of parkinsonism and of spastic skeletal muscle disorders |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3222392A (en) * | 1961-09-28 | 1965-12-07 | Frank M Berger | N-methyl 2,2-diphenyl-3-hydroxypropyl carbamate |
US4551473A (en) * | 1984-04-26 | 1985-11-05 | Schossow George W | Method of inhibiting snoring and obstructive sleep apnea |
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1957
- 1957-03-22 US US647756A patent/US2991225A/en not_active Expired - Lifetime
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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US3222392A (en) * | 1961-09-28 | 1965-12-07 | Frank M Berger | N-methyl 2,2-diphenyl-3-hydroxypropyl carbamate |
US4551473A (en) * | 1984-04-26 | 1985-11-05 | Schossow George W | Method of inhibiting snoring and obstructive sleep apnea |
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