US3036954A - Analgesic compositions - Google Patents
Analgesic compositions Download PDFInfo
- Publication number
- US3036954A US3036954A US844173A US84417359A US3036954A US 3036954 A US3036954 A US 3036954A US 844173 A US844173 A US 844173A US 84417359 A US84417359 A US 84417359A US 3036954 A US3036954 A US 3036954A
- Authority
- US
- United States
- Prior art keywords
- propoxyphene
- phenaglycodol
- weight
- analgesic
- parts
- 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
- 239000000203 mixture Substances 0.000 title claims description 17
- 230000000202 analgesic effect Effects 0.000 title description 7
- 229960004193 dextropropoxyphene Drugs 0.000 claims description 19
- XLMALTXPSGQGBX-GCJKJVERSA-N dextropropoxyphene Chemical compound C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 XLMALTXPSGQGBX-GCJKJVERSA-N 0.000 claims description 19
- HTYIXCKSEQQCJO-UHFFFAOYSA-N phenaglycodol Chemical compound CC(C)(O)C(C)(O)C1=CC=C(Cl)C=C1 HTYIXCKSEQQCJO-UHFFFAOYSA-N 0.000 claims description 15
- 229950005116 phenaglycodol Drugs 0.000 claims description 15
- 230000001225 therapeutic effect Effects 0.000 claims description 7
- 229920002472 Starch Polymers 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 239000002775 capsule Substances 0.000 description 3
- 239000007891 compressed tablet Substances 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 description 2
- 241000237858 Gastropoda Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000000730 antalgic agent Substances 0.000 description 2
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- -1 propionoxy 3 methyl-4-dimethylaminobutane Chemical compound 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 230000002936 tranquilizing effect Effects 0.000 description 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 229960004126 codeine Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- CPJSUEIXXCENMM-UHFFFAOYSA-N phenacetin Chemical compound CCOC1=CC=C(NC(C)=O)C=C1 CPJSUEIXXCENMM-UHFFFAOYSA-N 0.000 description 1
- 229960003893 phenacetin Drugs 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
Classifications
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
-
- 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
-
- 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
- A61K31/14—Quaternary ammonium compounds, e.g. edrophonium, choline
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/485—Morphinan derivatives, e.g. morphine, codeine
-
- 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
- A61K31/60—Salicylic acid; Derivatives thereof
-
- 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
- A61K31/60—Salicylic acid; Derivatives thereof
- A61K31/618—Salicylic acid; Derivatives thereof having the carboxyl group in position 1 esterified, e.g. salsalate
- A61K31/621—Salicylic acid; Derivatives thereof having the carboxyl group in position 1 esterified, e.g. salsalate having the hydroxy group in position 2 esterified, e.g. benorylate
Definitions
- d-propoxyphene identified chemically as a-d-LZ-diphenyl 2 propionoxy 3 methyl-4-dimethylaminobutane
- a-d-LZ-diphenyl 2 propionoxy 3 methyl-4-dimethylaminobutane is an efiiective analgesic agent.
- it has been extensively used, generally in oral dosage form, for the relief of pain.
- analgesic activity of d-propoxyphene is enhanced and prolonged if there is combined with the d-propoxyphene an amount of phenaglycodol, 2- p-chlorophenyl-3-methyl-2,3-butanediol.
- the potentiation of the analgesic effectiveness of d-propoxyphene by means of pheuaglycodol is quite surprising since the latter compound is a tranquilizing agent with no observable analgesic activity.
- the amount of phenaglycodol required for the potentiation of the d-propoxyphene is less than the dose amount customarily used for tranquilizing response.
- the phenaglycodol and dpropoxyphene are combined in a weight ratio upwards of about 3 parts of phenaglycodol to 1 part of d-propoxyphene.
- the presently preferred ratio is about 5 parts by weight of phenaglycodol to 1 part by weight of dpropoxyphene.
- a higher ratio for example, a 7 to 1 ratio, can be employed, but ratios above this value are generally not desirable since the higher ratios provide an amount of phenaglycodol sufiicient to evoke a marked tranquilizing response.
- elTect may be desirable in certain instances, such is not usually the case.
- the d-propoxyphene-phenaglycodol compositions of this invention can be employed in any of the usual therapeutic dosage forms such as filled capsules, compressed tablets, elixirs, suspensions, and the like.
- filled capsules and compressed tablets are the preferred pharmaceutical forms, and such are readily compounded using the customary excipients and extending media.
- the d-propoxyphene can be employed in the form of its free base, but generally is employed in the form of a nontoxic acid addition salt since the latter is more amenable to formulation.
- active therapeutic ingredients can be associated with the novel compositions of this invention, 'such ingredients generally being analgesic agents, for example, acetylsalicylic acid, acetophenetidine, codeine, and the like.
- the d-propoxyphene can be used a dose amount less than that customarily required.
- An illustrative composition suitable for filling into telescoping gelatin capsules is prepared by thoroughly mixing 1 part by weight of d-propoxyphene hydrochloride, 5 parts by weight of phenaglycodol, and 1.3 parts by weight of starch. The mixture is filled into telescoping gelatin capsules of such size that each capsule contains about 32 mg. of d-propoxyphene hydrochloride.
- composition can be made up to contain about 10 parts by weight of acetylsalicylic acid, in which case each 32 mg. dose of d-propoxyphene hydrochloride will provide about 320 mg. of acetylsalicylic acid.
- composition suitable for the preparation of compressed tablets is made up of the following ingredients in the amounts shown:
- d-Propoxyphene hydrochloride 7 Phenaglycodol 35 M agnesium stearate 1
- the d-propoxyphene hydrochloride and phenaglycodol and half the amounts of the starch and magnesium stearate are thoroughly mixed and are compressed into slugs.
- the slugs are sieved through a No. 12 screen.
- the remainder of the starch and magnesium stearate is then mixed with the screened material and the mixture is compressed on a standard tabletting machine into tablets of such size that each tablet contains about 32 mg. of d-propoxyphene hydrochloride.
- a therapeutic composition comprising about 1 part by weight of d-propoxyphene and from about 3 to about 7 parts by weight of phenaglycodol.
- a therapeutic composition comprising about 1 part by weight of d-propoxyphene to about 5 parts by weight of phenaglycodol.
- a therapeutic composition in dosage unit form comprising about 32 mg. of d-propoxyphene in the form of its hydrochloric acid addition salt and about mg. of phenaglycodol.
Description
United States Patent Office 3,036,954 Patented May 29, 1962 3,036,954 ANALGESIC COMPOSITIONS Enos Brown Robbins, Indianapolis, Ind., assignor to Eli Lilly and Company, Indianapolis, Ind., a corporation of Indiana No Drawing. Filed Oct. 5, 1959, Ser. No. 844,173 3 Claims. (Cl. 167-65) This invention relates to novel analgesic compositions.
It is known that d-propoxyphene, identified chemically as a-d-LZ-diphenyl 2 propionoxy 3 methyl-4-dimethylaminobutane, is an efiiective analgesic agent. As such, it has been extensively used, generally in oral dosage form, for the relief of pain.
I have discovered that the analgesic activity of d-propoxyphene is enhanced and prolonged if there is combined with the d-propoxyphene an amount of phenaglycodol, 2- p-chlorophenyl-3-methyl-2,3-butanediol. The potentiation of the analgesic effectiveness of d-propoxyphene by means of pheuaglycodol is quite surprising since the latter compound is a tranquilizing agent with no observable analgesic activity. Furthermore, the amount of phenaglycodol required for the potentiation of the d-propoxyphene is less than the dose amount customarily used for tranquilizing response.
For etfective potentiation the phenaglycodol and dpropoxyphene are combined in a weight ratio upwards of about 3 parts of phenaglycodol to 1 part of d-propoxyphene. The presently preferred ratio is about 5 parts by weight of phenaglycodol to 1 part by weight of dpropoxyphene. A higher ratio, for example, a 7 to 1 ratio, can be employed, but ratios above this value are generally not desirable since the higher ratios provide an amount of phenaglycodol sufiicient to evoke a marked tranquilizing response. Although that elTect may be desirable in certain instances, such is not usually the case.
As is the case with therapeutic compositions of dpropoxyphene, the d-propoxyphene-phenaglycodol compositions of this invention can be employed in any of the usual therapeutic dosage forms such as filled capsules, compressed tablets, elixirs, suspensions, and the like. For reasons of convenience of administration and stability, filled capsules and compressed tablets are the preferred pharmaceutical forms, and such are readily compounded using the customary excipients and extending media.
The d-propoxyphene can be employed in the form of its free base, but generally is employed in the form of a nontoxic acid addition salt since the latter is more amenable to formulation.
If desired, other active therapeutic ingredients can be associated with the novel compositions of this invention, 'such ingredients generally being analgesic agents, for example, acetylsalicylic acid, acetophenetidine, codeine, and the like.
By virtue of the potentiating efiect of the phenaglycodol, the d-propoxyphene can be used a dose amount less than that customarily required. However, it is preferable to employ in my novel compositions the usual dose amount of d-propoxyphene, thereby to obtain a more pronounced analgesic action than is otherwise obtainable.
An illustrative composition suitable for filling into telescoping gelatin capsules is prepared by thoroughly mixing 1 part by weight of d-propoxyphene hydrochloride, 5 parts by weight of phenaglycodol, and 1.3 parts by weight of starch. The mixture is filled into telescoping gelatin capsules of such size that each capsule contains about 32 mg. of d-propoxyphene hydrochloride.
If desired, the foregoing composition can be made up to contain about 10 parts by weight of acetylsalicylic acid, in which case each 32 mg. dose of d-propoxyphene hydrochloride will provide about 320 mg. of acetylsalicylic acid.
An illustrative composition suitable for the preparation of compressed tablets is made up of the following ingredients in the amounts shown:
Parts by weight d-Propoxyphene hydrochloride 7 Phenaglycodol 35 M agnesium stearate 1 The d-propoxyphene hydrochloride and phenaglycodol and half the amounts of the starch and magnesium stearate are thoroughly mixed and are compressed into slugs. The slugs are sieved through a No. 12 screen. The remainder of the starch and magnesium stearate is then mixed with the screened material and the mixture is compressed on a standard tabletting machine into tablets of such size that each tablet contains about 32 mg. of d-propoxyphene hydrochloride.
I claim:
1. A therapeutic composition comprising about 1 part by weight of d-propoxyphene and from about 3 to about 7 parts by weight of phenaglycodol.
2. A therapeutic composition comprising about 1 part by weight of d-propoxyphene to about 5 parts by weight of phenaglycodol.
3. A therapeutic composition in dosage unit form comprising about 32 mg. of d-propoxyphene in the form of its hydrochloric acid addition salt and about mg. of phenaglycodol.
Starch powder References Cited in the file of this patent UNITED STATES PATENTS Pohland Dec. 27, 1955 OTHER REFERENCES
Claims (1)
1. A THERAPEUTIC COMPOSITION COMPRISING ABOUT 1 PART BY WEIGHT OF D-PROPOXYPHENE AND FROM ABOUT 3 TO ABOUT 7 PARTS BY WEIGHT OF PHENAGLYCODOL.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US844173A US3036954A (en) | 1959-10-05 | 1959-10-05 | Analgesic compositions |
| ES0256358A ES256358A1 (en) | 1959-10-05 | 1960-03-08 | Analgesic compositions |
| BE589578A BE589578A (en) | 1959-10-05 | 1960-04-08 | Process for the preparation of an improved analgesic compound and product thus obtained |
| FR821408A FR300M (en) | 1959-10-05 | 1960-08-26 | Improved analgesic composition. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US844173A US3036954A (en) | 1959-10-05 | 1959-10-05 | Analgesic compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3036954A true US3036954A (en) | 1962-05-29 |
Family
ID=25292022
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US844173A Expired - Lifetime US3036954A (en) | 1959-10-05 | 1959-10-05 | Analgesic compositions |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3036954A (en) |
| BE (1) | BE589578A (en) |
| ES (1) | ES256358A1 (en) |
| FR (1) | FR300M (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3131122A (en) * | 1961-04-14 | 1964-04-28 | Boehringer Sohn Ingelheim | Method of producing analgesia with n-substituted-4-phenyl-4-carbalkoxypiperidines |
| US3141024A (en) * | 1964-07-14 | S-trimethoxy benzoyl amino | ||
| US3225098A (en) * | 1961-07-19 | 1965-12-21 | Hoechst Ag | N-substituted phenylalkylamines |
| US3247222A (en) * | 1962-12-26 | 1966-04-19 | Robins Co Inc A H | Alpha (nu-hydrocarbonpyrrolidyl-3-) alpha, alpha carbocyclic arylacetamides |
| US3248418A (en) * | 1962-06-26 | 1966-04-26 | Charles D Bossinger | 2-hydroxy-2-phenyl alkyl carbamates |
| US3265728A (en) * | 1962-07-18 | 1966-08-09 | Armour Pharma | Substituted phenethyl carbamates |
| US3265727A (en) * | 1962-06-26 | 1966-08-09 | Armour Pharma | Phenyl alkyl-1, 2 dicarbamates |
| US3278380A (en) * | 1962-02-06 | 1966-10-11 | Armour Pharma | Methods of calming employing diphenyl hydroxy carbamate compounds |
| US3402244A (en) * | 1962-12-26 | 1968-09-17 | Robins Co Inc A H | Analgesic and anti-inflammatory methods and compositions |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2728779A (en) * | 1952-12-03 | 1955-12-27 | Lilly Co Eli | Esters of substituted aminobutanes |
-
1959
- 1959-10-05 US US844173A patent/US3036954A/en not_active Expired - Lifetime
-
1960
- 1960-03-08 ES ES0256358A patent/ES256358A1/en not_active Expired
- 1960-04-08 BE BE589578A patent/BE589578A/en unknown
- 1960-08-26 FR FR821408A patent/FR300M/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2728779A (en) * | 1952-12-03 | 1955-12-27 | Lilly Co Eli | Esters of substituted aminobutanes |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3141024A (en) * | 1964-07-14 | S-trimethoxy benzoyl amino | ||
| US3131122A (en) * | 1961-04-14 | 1964-04-28 | Boehringer Sohn Ingelheim | Method of producing analgesia with n-substituted-4-phenyl-4-carbalkoxypiperidines |
| US3225098A (en) * | 1961-07-19 | 1965-12-21 | Hoechst Ag | N-substituted phenylalkylamines |
| US3278380A (en) * | 1962-02-06 | 1966-10-11 | Armour Pharma | Methods of calming employing diphenyl hydroxy carbamate compounds |
| US3248418A (en) * | 1962-06-26 | 1966-04-26 | Charles D Bossinger | 2-hydroxy-2-phenyl alkyl carbamates |
| US3265727A (en) * | 1962-06-26 | 1966-08-09 | Armour Pharma | Phenyl alkyl-1, 2 dicarbamates |
| US3265728A (en) * | 1962-07-18 | 1966-08-09 | Armour Pharma | Substituted phenethyl carbamates |
| US3247222A (en) * | 1962-12-26 | 1966-04-19 | Robins Co Inc A H | Alpha (nu-hydrocarbonpyrrolidyl-3-) alpha, alpha carbocyclic arylacetamides |
| US3402244A (en) * | 1962-12-26 | 1968-09-17 | Robins Co Inc A H | Analgesic and anti-inflammatory methods and compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| ES256358A1 (en) | 1960-06-16 |
| BE589578A (en) | 1960-10-10 |
| FR300M (en) | 1961-03-13 |
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