US2990328A - Stable therapeutic compositions containing acetylsalicylic acid-anhydride - Google Patents
Stable therapeutic compositions containing acetylsalicylic acid-anhydride Download PDFInfo
- Publication number
- US2990328A US2990328A US729258A US72925858A US2990328A US 2990328 A US2990328 A US 2990328A US 729258 A US729258 A US 729258A US 72925858 A US72925858 A US 72925858A US 2990328 A US2990328 A US 2990328A
- Authority
- US
- United States
- Prior art keywords
- anhydride
- acid
- milligrams
- acetylsalicylic
- asa
- 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
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
- A61K31/60—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
-
- 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
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/42—Phosphorus; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/02—Inorganic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
- A61K47/183—Amino acids, e.g. glycine, EDTA or aspartame
Definitions
- Acetylsalicylic acid is known to decompose to the irritating compounds
- acetic and salicylic acids are known to be an irritant to the gastric mucosa.
- An additional object is to provide such compositions which do not form irritating amounts of acetic and salicylic acids in the stomach after oral administration.
- a further object is to provide such compositions which are free from mucosal irritation side-effects.
- a still further object is to provide such compositions which are stable under manufacturing and storage conditions.
- 'Ilheterm" dosage unit form refers to physically discrete units suitable as unitary dosages for human subjects, each unit containing a predetermined quantity of active material calculated to produ ce the desired therapeutic effect in association with the required pharmaceutical diluent or carrier.
- the specificationsfor the novel dosage unit forms of this invention are dictated by and directly dependent upon (a) the unique characteristics of the active material and the particulartherapeutic effect to be achieved and (b) the limitations inherent in the art of compounding such an active material for therapeutic use in human beings, as disclosed in detail in this specification, being features of the present invention.
- suitable solid oral dosage unit forms in accord with this invention are a tablet, a capsule, a pill, a powder packet, an effervescent granule, a pilule, a Water, a chewing gum, a cachet, a pellet, multiples of any of the foregoing, when segregated as a single dose.
- forms known as the sustained-release, delayed action or enteric types are included.
- the basic method of preparing, the desired dosage unit form comprises mixing the active ingredient [acetylsalh cylic acid] anhydride with an appropriate diluent including. an appropriate acidic substance and preparing the dosage unit form by methods and with means known in the 'art.
- nonalkaline is intended to mean neutral and acidic.
- Other than'neutral and acidic, i.e., alkaline conditions have been found to hasten deterioration of the active ingredient, [acetylsalicylic acidJ-anhydride.
- alkaline conditions have been found to hasten deterioration of the active ingredient, [acetylsalicylic acidJ-anhydride.
- alkaline conditions have been found to hasten deterioration of the active ingredient, [acetylsalicylic acidJ-anhydride.
- alkaline deterioration is more pronounced at temperatures above 25 degrees centigrade.
- the experimental data show that the presence of water is a problem both in the bulk mixtures used for manufacturing and in the final dosage unit forms. While deterionation from the presence of water is not immediately ittsm b e i s e u i fa ms h t ees c grade, the data at temperatures above 25 degrees centigrade indicate that long-term stability at 25 degrees centigrade and short-term stability at temperatures above 25 degrees centigrade would be unsatisfactory. Thus, for long-term stability at 25 degrees centigradeand shortterm stability above 25 degrees centigrade, substantially anhydrous dosage unit forms are preferred.
- diluen is used in reference to pharmaceutically acceptable carriers, bulking agents, excipients, binders, lubricants, adhesives, disintegrators, stabilizers (e.g., acidic substances infraland the like, for example: starch, talc, sucrose, dicalcium phosphate, lactose, sorbitol, 'mannitol, Thixcin (ajhighly saturated castor oil), mixtures of the foregoing, andthe. like.
- pharmaceutically acceptable carriers bulking agents, excipients, binders, lubricants, adhesives, disintegrators, stabilizers (e.g., acidic substances infraland the like, for example: starch, talc, sucrose, dicalcium phosphate, lactose, sorbitol, 'mannitol, Thixcin (ajhighly saturated castor oil), mixtures of the foregoing, andthe. like.
- acidic substances for. example: citric acid; ascorbic, acid, alkali metal bitartrates, alkali metal biphosphates, tartaric acid, malic acid, glutamic acid hydrochloride, pyridoxine hydrochloride, nicotinic acid, acidic amino acids, salts of amino acids, succinic acid, glucuronic acid, glutaric acid, pimelic acid, malonic acid, mandelic acid, adipic acid, tricarballylie acid, mixtures of the foregoing, and the like, From among this, group sodium biphosphate, citric acid, pyridoxine hydrochloride, tartaric acid and malic acid are preferred.
- the amount of [acetylsalicyclio acidl-anhydride can be varied over a considerable range. From about 25 milligrams to about 1000 milligrams per dosage unit form can be utilized, with from about sixty milligrams to about 400 milligrams preferred. The smaller amounts are preferred in the dosage unit forms for children. The higher dosages are most useful in the rheumatic type diseases.
- compositions of this invention can be added to the compositions of this invention.
- active ingredients are the following: acetophenetidin, caifeine, codeine and its salts, salicylamide, N-acetyl-para-aminophenol, anti-inflammatory steroids, for example, cortisone, hydrocortisone, 6-methyl-delta-1- hydrocortisone, prednisone, prednisolone, their esters and the salts of acid esters thereof, and like derivatives.
- ditional illustrative examples are the following: tranquilizers, antihistaminics, antitussive agents, antibiotics, sedatives and vitamins.
- compositions of this invention possess analgesic
- antipyretic and antirheumatic properties are useful in therelated afilictions and disorders susceptible to such properties.
- ASA acetylsalicylic acid. sterotex hydrogenated vegetable 011.
- ASA acetylsalicylic acid
- ASA acetylsalicy1ic acid
- Table V contains the data on stability ofrnixtures consisting of [acetylsalicyclic acidl anhydrideand various acidic substances and stored in soft glass" containers. The mixtures were prepared by gr-anulating thirty grams ofscrew caps.
- the data in Table V show the superior stability of 8
- the granulation is prepared bymixing the [acetylsalicyliclzanhydridewith the sorbi'toli-starch paste, which contains the citric acid dissolved in the water, and drying the mixture, at about 120 degrees Fahrenheit for ten to a twenty hours. After'milling and screening, the granulation is mixedithoroughly with the starch-talc lubricant and-compressedinto tablets. Clinical testing shows that these tablets, each containing 300 milligrams of [acetylsalicylic acid]-anhydride, do not causegastric irritation and provide superior blood levels of salicylate including the esterified compound, acetylsalicylic acid.
- an anti-inflammatory steriod for example, 6-methyl-prednisolone, about 0.15 to about 4 milligrams; cortisone acetate, about 2.5 to about milligrams; hydrocortisone acetate, about 2 to about 20'mi1ligrams; prednisone, about 0.25 to about 5 milligrams; 6-fluoro-hydrocortisone, about 0.15 to about 4 milligrams; 6-fluoro-prednisolone,. about 0.15 to about 4 milligrams; gives a composition useful in arthritic affiictions.
- tablets containing 60, 160, 400, 600 and 1000 milligrams of [-acetylsalicylic acidl-anhydride can be prepared through substituting the 7500 grams of the a.n-.
- Table VI contains the data on stability of mixtures consisting of [acetylsalicyclic acid] -anhydride and various amounts of citric acid. The mixtures were prepared as in Table V. i
- the illustrative example contains citric acid, one of the five preferred acidic substances the others being malic acid, pyridoxine hydrochloride, sodium biphosphate and tartaric acid.
- the preferred amount of said acidic substances is from about one to about fifty milligrams per 300 milligrams of [-acetylsalicyclic acidl-anhydride.
- tarqhiho isd e "-9-"? 403.
- Eight to ten successive coatings are applied to give a gum containing fifty milligrams of acetylsalicylic acid] -anhydride.
- a second dusting with the hydrogenated castor oil is applied.
- the final finishing and protective coatings contain flavor, coloring and polishing ingredients. It is preferred to apply a final water-proof-preservative type of coating, for example, carnauba Wax.
- Each packet contains:
- EXAMPLE Hard-filled capsule Following the procedure of Example 2, capsules are prepared containing 228 milligrams of [acetylsalicylic acidJ-anhydride from 70 to 160 milligrams of acetophenetidin and from sixteen to 35 milligrams of cafieine per capsule.
- EXAMPLE 6 Compressed tablet Following the procedure of Example 1, tablets are prepared with a complementary active ingredient by adding to 30 milligrams of codeine sulfate per 300 milligrams of [acetylsalicylic acid]-anhydride, granulating and compressing by the method shown.
- EXAMPLE 9 Hard-filled capsule Following the procedure of Example 2, capsules are prepared with a complementary active ingredient by adding 1 to 4 milligrams of chlorpheniramine maleate per capsule.
- Milligrams [Acetylsalicylic acidJ-anhydride 300 6-methyl prednisolnne 1 Citric acid 10 Ascorbic acid, ten milligrams per tablet, can be added to the above formula.
- a stable, solid oral therapeutic preparation in dosage unit form comprising [acetylsalicylic acid] -anhydride and apharmaceutically acceptable non-alkaline diluentcontaining from about 0.3 to about 17% by weight ofsaid anyhdride of a pharmaceutically-acceptable acid-reacting stabilizing compound to stabilize the preparation against decomposition by alkali, which diluent does not lower substantially the melting point of said anhydride.
- a substantially anhydrous, stable, solid oral therapeutic preparation in dosage unit form comprising [acetylsalicylic acid]-anhydride and a pharmaceutically acceptable non-alkaline diluent containing from about 0.3 to about 17% by weight of said anhydride of a pharmaceutically-acceptable acid-reacting stabilizing compound to stabilize the preparation against decomposition by alkali, which diluent does not lower substantially the melting point of said anhydride.
- a stable, solid oral therapeutic preparation in dosage unit form comprising from about 25 to about 1000 milligrams of [acetylsalicylic acidJ-anhydride and a pharmaceutically acceptable non-alkaline diluent containing from about 0.3 to about 17% by weight of said anhydride of a pharmaceutically-acceptable acid-reacting stabilizing compound to stabilize the preparation against decomposition by alkali, which diluent does not lower substantially the melting point of said anhydride.
- a substantially anhydrous, stable, solid oral therapeutic preparation in dosage unit form comprising from about sixty to about 400 milligrams of [acetylsalicylic acidJ-anhydride and a pharmaceutically acceptable istlkaline diluent containing from about 0.3 to about 17% by weight of said anhydride of a pharmaceutically-acceptable acid-reacting stabilizing compound to stabilize the preparation against decomposition by alkali, which diluent does not lower substantially the melting point of said anhydride.
- a substantially anhydrous, stable solid oral therapeutic preparation in dosage unit form comprising an antiinflammatory steroid, from about sixty to about 400 milligrams of [acetylsalicylic acid]-anl1ydride and a pharmaceutically acceptable non-alkaline diluent containing from about 0.3 to about 17% by weight of said anhydride of a pharmaceutically-acceptable acid-reacting stabilizing compound to stabilize the preparation against decomposition by alkali, which diluent does not lower substantially the melting point of said anhydride.
- a substantially anhydrous stable, oral therapeutic tablet comprising from about 0.15 to about four milligrams of 6-methylprednisolone, from about sixty to about 400 milligrams of [acetylsalicylic acid] -anhydride and a pharmaceutically acceptable non-alkaline diluent containing from about 0.3 to about 17% by weight of said anhydride of a pharmaceutically-acceptable acid-reacting stabilizing compound to stabilize the preparation against decomposition by alkali, which diluent does not lower substantially the melting point of said anhydride.
- a substantially anhydrous stable, oral therapeutic tablet comprising one milligram of -methylprednisolone, 300 milligrams of [acetylsalicylic acid]-anhydride and a pharmaceutically acceptable non-alkaline diluent containing from about 0.3 to about 17% by weight of said anhydride of a pharmaceutically-acceptable acid-reacting stabilizing compound to stabilize the preparation against decomposition by alkali, which diluent does not lower substantially the melting point of said anhydride.
- a stable, solid oral therapeutic preparation in dosage unit form comprising [acetylsalicylic acid] -anhydride and a pharmaceutically acceptable non-alkaline diluent containing from about 0.3 to about 17% by weight of said anhydride of an acid-reacting substance selected from the group consisting of citric acid, ascorbic acid, alkali metal bitartrates, alkali metal biphosphates, tartaric acid, malic acid, glutamic acid hydrochloride, pyridoxine hydrochloride, nicotinic acid, acidic amino acids, salts of amino acids, succinic acid, glucuronic acid, glutaric acid, pimelic acid, malonic acid, mandelic acid, adipic acid, tri- CatballYliCf acid, and mixtures "(.hereof',which diluent dbes notzlower i 'substnti'allythea melting point ofsaid aphy dri iei;
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Inorganic Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL245245D NL245245A (sv) | 1958-04-18 | ||
NL121097D NL121097C (sv) | 1958-04-18 | ||
BE585778D BE585778A (sv) | 1958-04-18 | ||
US729258A US2990328A (en) | 1958-04-18 | 1958-04-18 | Stable therapeutic compositions containing acetylsalicylic acid-anhydride |
GB9597/59A GB885081A (en) | 1958-04-18 | 1959-03-19 | Improvements in or relating to therapeutic compositions containing (acetylsalicylic acid)-anhydride |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US729258A US2990328A (en) | 1958-04-18 | 1958-04-18 | Stable therapeutic compositions containing acetylsalicylic acid-anhydride |
Publications (1)
Publication Number | Publication Date |
---|---|
US2990328A true US2990328A (en) | 1961-06-27 |
Family
ID=24930248
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US729258A Expired - Lifetime US2990328A (en) | 1958-04-18 | 1958-04-18 | Stable therapeutic compositions containing acetylsalicylic acid-anhydride |
Country Status (4)
Country | Link |
---|---|
US (1) | US2990328A (sv) |
BE (1) | BE585778A (sv) |
GB (1) | GB885081A (sv) |
NL (2) | NL121097C (sv) |
Cited By (31)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3495001A (en) * | 1968-05-27 | 1970-02-10 | Miles Lab | Effervescent compositions of acetylsalicylic acid |
US4028239A (en) * | 1973-06-03 | 1977-06-07 | Lonza Ltd. | Process for preventing lime deposits in a humidifier |
US4294819A (en) * | 1980-08-18 | 1981-10-13 | Bristol-Myers Company | Alkaline analgesic capsule |
EP0045238A2 (en) * | 1980-07-29 | 1982-02-03 | Sanofi S.A. | Acid stabilized compositions of thieno-pyridine derived compounds and process for preventing degradation of such compounds |
US4339428A (en) * | 1980-08-18 | 1982-07-13 | Bristol-Myers Company | Capsule product containing high dosage of aspirin in powder or granulated form and alkaline tablet or pellet comprising magnesium carbonate, calcium carbonate and a magnesium dry component |
US4900559A (en) * | 1985-12-12 | 1990-02-13 | Briston-Myers Company | Stabilized enteric coated aspirin granules and process of preparation |
WO2001049124A1 (en) * | 1999-12-30 | 2001-07-12 | Wm. Wrigley Jr. Company | Release of lipophilic active agents from chewing gum |
US6290985B2 (en) | 1999-04-06 | 2001-09-18 | Wm. Wrigley, Jr. Company | Over-coated chewing gum formulations including tableted center |
US6350480B1 (en) * | 1999-12-30 | 2002-02-26 | Wm. Wrigley Jr. Company | Chewing gum product including a hydrophilic gum base and method of producing |
US6355265B1 (en) | 1999-04-06 | 2002-03-12 | Wm. Wrigley Jr. Company | Over-coated chewing gum formulations |
US6444241B1 (en) | 2000-08-30 | 2002-09-03 | Wm. Wrigley Jr. Company | Caffeine coated chewing gum product and process of making |
US20020159956A1 (en) * | 1999-04-06 | 2002-10-31 | Ream Ronald L. | Over-coated chewing gum formulations |
US20020164398A1 (en) * | 1998-12-15 | 2002-11-07 | Johnson Sonya S. | Method and product for accelerating absorption of medicaments through oral mucosa |
US6531114B1 (en) | 1999-04-06 | 2003-03-11 | Wm. Wrigley Jr. Company | Sildenafil citrate chewing gum formulations and methods of using the same |
US6541048B2 (en) | 1999-09-02 | 2003-04-01 | Wm. Wrigley Jr. Company | Coated chewing gum products containing an acid blocker and process of preparing |
US6569472B1 (en) | 2000-09-01 | 2003-05-27 | Wm. Wrigley Jr. Company | Coated chewing gum products containing antacid and method of making |
US6572900B1 (en) | 2000-06-09 | 2003-06-03 | Wm. Wrigley, Jr. Company | Method for making coated chewing gum products including a high-intensity sweetener |
US6579545B2 (en) | 2000-12-22 | 2003-06-17 | Wm. Wrigley Jr. Company | Coated chewing gum products containing an antigas agent |
US6586023B1 (en) | 1998-12-15 | 2003-07-01 | Wm. Wrigley Jr. Company | Process for controlling release of active agents from a chewing gum coating and product thereof |
US6627234B1 (en) | 1998-12-15 | 2003-09-30 | Wm. Wrigley Jr. Company | Method of producing active agent coated chewing gum products |
US6645535B2 (en) | 1999-09-02 | 2003-11-11 | Wm. Wrigley Jr. Company | Method of making coated chewing gum products containing various antacids |
US6663849B1 (en) | 2000-09-01 | 2003-12-16 | Wm. Wrigley Jr. Company | Antacid chewing gum products coated with high viscosity materials |
US6773716B2 (en) | 1999-04-06 | 2004-08-10 | Wm. Wrigley Jr. Company | Over-coated chewing gum formulations |
US20040185144A1 (en) * | 2000-06-09 | 2004-09-23 | Witkewitz David L. | Method for making coated chewing gum products with a coating including an aldehyde flavor and a dipeptide sweetener |
US6949264B1 (en) | 1996-11-27 | 2005-09-27 | Wm. Wrigley Jr. Company | Nutraceuticals or nutritional supplements and method of making |
US20060141008A1 (en) * | 1999-04-06 | 2006-06-29 | Ream Ronald L | Over-coated product including consumable center and medicament |
US20100104620A1 (en) * | 1999-04-06 | 2010-04-29 | Wm. Wrigley Jr. Company | Over-coated product including tableted center and medicament |
US8679522B2 (en) | 1999-09-20 | 2014-03-25 | Jack Barreca | Chewing gum |
US9253991B2 (en) | 1999-09-20 | 2016-02-09 | Jack Barreca | Chewing gum with B vitamins |
US9387168B2 (en) | 1999-09-20 | 2016-07-12 | Jack Barreca | Chewing gum with tomatidine |
US20190350946A1 (en) * | 2017-08-04 | 2019-11-21 | Poli Md S.R.L. | Medical Device for the Treatment of HPV Cutaneous Infections |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US922766A (en) * | 1907-10-31 | 1909-05-25 | Farbenfab Vorm Bayer F & Co | Anhydrid of acyl salicylic acid. |
US2888382A (en) * | 1957-10-28 | 1959-05-26 | Upjohn Co | Therapeutic composition and process |
-
0
- BE BE585778D patent/BE585778A/xx unknown
- NL NL245245D patent/NL245245A/xx unknown
- NL NL121097D patent/NL121097C/xx active
-
1958
- 1958-04-18 US US729258A patent/US2990328A/en not_active Expired - Lifetime
-
1959
- 1959-03-19 GB GB9597/59A patent/GB885081A/en not_active Expired
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US922766A (en) * | 1907-10-31 | 1909-05-25 | Farbenfab Vorm Bayer F & Co | Anhydrid of acyl salicylic acid. |
US2888382A (en) * | 1957-10-28 | 1959-05-26 | Upjohn Co | Therapeutic composition and process |
Cited By (40)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3495001A (en) * | 1968-05-27 | 1970-02-10 | Miles Lab | Effervescent compositions of acetylsalicylic acid |
US4028239A (en) * | 1973-06-03 | 1977-06-07 | Lonza Ltd. | Process for preventing lime deposits in a humidifier |
EP0045238A2 (en) * | 1980-07-29 | 1982-02-03 | Sanofi S.A. | Acid stabilized compositions of thieno-pyridine derived compounds and process for preventing degradation of such compounds |
EP0045238A3 (en) * | 1980-07-29 | 1983-02-16 | Sanofi, Societe Anonyme | Acid stabilized compositions of thieno-pyridine derived compounds and process for preventing degradation of such compounds |
US4294819A (en) * | 1980-08-18 | 1981-10-13 | Bristol-Myers Company | Alkaline analgesic capsule |
US4339428A (en) * | 1980-08-18 | 1982-07-13 | Bristol-Myers Company | Capsule product containing high dosage of aspirin in powder or granulated form and alkaline tablet or pellet comprising magnesium carbonate, calcium carbonate and a magnesium dry component |
US4900559A (en) * | 1985-12-12 | 1990-02-13 | Briston-Myers Company | Stabilized enteric coated aspirin granules and process of preparation |
US6949264B1 (en) | 1996-11-27 | 2005-09-27 | Wm. Wrigley Jr. Company | Nutraceuticals or nutritional supplements and method of making |
US7163705B2 (en) | 1998-12-15 | 2007-01-16 | Wm. Wrigley Jr. Company | Coated chewing gum product and method of making |
US6627234B1 (en) | 1998-12-15 | 2003-09-30 | Wm. Wrigley Jr. Company | Method of producing active agent coated chewing gum products |
US6592850B2 (en) | 1998-12-15 | 2003-07-15 | Wm. Wrigley Jr. Company | Sildenafil citrate chewing gum formulations and methods of using the same |
US20020164398A1 (en) * | 1998-12-15 | 2002-11-07 | Johnson Sonya S. | Method and product for accelerating absorption of medicaments through oral mucosa |
US6586023B1 (en) | 1998-12-15 | 2003-07-01 | Wm. Wrigley Jr. Company | Process for controlling release of active agents from a chewing gum coating and product thereof |
US20100104620A1 (en) * | 1999-04-06 | 2010-04-29 | Wm. Wrigley Jr. Company | Over-coated product including tableted center and medicament |
US6322806B1 (en) | 1999-04-06 | 2001-11-27 | Wm. Wrigley Jr. Company | Over-coated chewing gum formulations including tableted center |
US6465003B2 (en) | 1999-04-06 | 2002-10-15 | Wm. Wrigley Jr. Company | Over-coated chewing gum formulations |
US6531114B1 (en) | 1999-04-06 | 2003-03-11 | Wm. Wrigley Jr. Company | Sildenafil citrate chewing gum formulations and methods of using the same |
US20060141008A1 (en) * | 1999-04-06 | 2006-06-29 | Ream Ronald L | Over-coated product including consumable center and medicament |
US6558692B2 (en) | 1999-04-06 | 2003-05-06 | Wm. Wrigley Jr. Company | Over-coated chewing gum formulations |
US6773716B2 (en) | 1999-04-06 | 2004-08-10 | Wm. Wrigley Jr. Company | Over-coated chewing gum formulations |
US7935362B2 (en) | 1999-04-06 | 2011-05-03 | Wm. Wrigley Jr. Company | Over-coated product including consumable center and medicament |
US6290985B2 (en) | 1999-04-06 | 2001-09-18 | Wm. Wrigley, Jr. Company | Over-coated chewing gum formulations including tableted center |
US6355265B1 (en) | 1999-04-06 | 2002-03-12 | Wm. Wrigley Jr. Company | Over-coated chewing gum formulations |
US20020159956A1 (en) * | 1999-04-06 | 2002-10-31 | Ream Ronald L. | Over-coated chewing gum formulations |
US6645535B2 (en) | 1999-09-02 | 2003-11-11 | Wm. Wrigley Jr. Company | Method of making coated chewing gum products containing various antacids |
US6541048B2 (en) | 1999-09-02 | 2003-04-01 | Wm. Wrigley Jr. Company | Coated chewing gum products containing an acid blocker and process of preparing |
US9253991B2 (en) | 1999-09-20 | 2016-02-09 | Jack Barreca | Chewing gum with B vitamins |
US9387168B2 (en) | 1999-09-20 | 2016-07-12 | Jack Barreca | Chewing gum with tomatidine |
US8679522B2 (en) | 1999-09-20 | 2014-03-25 | Jack Barreca | Chewing gum |
US6350480B1 (en) * | 1999-12-30 | 2002-02-26 | Wm. Wrigley Jr. Company | Chewing gum product including a hydrophilic gum base and method of producing |
WO2001049124A1 (en) * | 1999-12-30 | 2001-07-12 | Wm. Wrigley Jr. Company | Release of lipophilic active agents from chewing gum |
US20040185144A1 (en) * | 2000-06-09 | 2004-09-23 | Witkewitz David L. | Method for making coated chewing gum products with a coating including an aldehyde flavor and a dipeptide sweetener |
US7115288B2 (en) | 2000-06-09 | 2006-10-03 | Wm. Wrigley Jr. Company | Method for making coated chewing gum products with a coating including an aldehyde flavor and a dipeptide sweetener |
US6572900B1 (en) | 2000-06-09 | 2003-06-03 | Wm. Wrigley, Jr. Company | Method for making coated chewing gum products including a high-intensity sweetener |
US6444241B1 (en) | 2000-08-30 | 2002-09-03 | Wm. Wrigley Jr. Company | Caffeine coated chewing gum product and process of making |
US6663849B1 (en) | 2000-09-01 | 2003-12-16 | Wm. Wrigley Jr. Company | Antacid chewing gum products coated with high viscosity materials |
US6569472B1 (en) | 2000-09-01 | 2003-05-27 | Wm. Wrigley Jr. Company | Coated chewing gum products containing antacid and method of making |
US6579545B2 (en) | 2000-12-22 | 2003-06-17 | Wm. Wrigley Jr. Company | Coated chewing gum products containing an antigas agent |
US20190350946A1 (en) * | 2017-08-04 | 2019-11-21 | Poli Md S.R.L. | Medical Device for the Treatment of HPV Cutaneous Infections |
US10993950B2 (en) * | 2017-08-04 | 2021-05-04 | Poli Md S.R.L. | Medical device for the treatment of HPV cutaneous infections |
Also Published As
Publication number | Publication date |
---|---|
BE585778A (sv) | |
NL245245A (sv) | |
NL121097C (sv) | |
GB885081A (en) | 1961-12-20 |
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