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US3924003A - Substituted or unsubstituted p-alkanoyl toluenes as anti-obesity and anti-diabetic agents - Google Patents

Substituted or unsubstituted p-alkanoyl toluenes as anti-obesity and anti-diabetic agents Download PDF

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US3924003A
US3924003A US546756A US54675675A US3924003A US 3924003 A US3924003 A US 3924003A US 546756 A US546756 A US 546756A US 54675675 A US54675675 A US 54675675A US 3924003 A US3924003 A US 3924003A
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obesity
compound
milligrams
alkanoyl
toluenes
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US546756A
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Robert S Ho
William J Houlihan
Jeffrey Nadelson
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Sandoz AG
Sandoz Inc
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Sandoz AG
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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
    • A61K31/12—Ketones

Definitions

  • This invention relates to the pharmaceutical activity of p-alkanoyl toluenes. More particularly, this invention concerns the use of substituted or unsubstituted palkanoyl toluenes in the treatment of obesity and diabetes. The invention also relates to pharmaceutical compositions containing these compounds as an active ingredient thereof.
  • the active agents with which this invention is conccrned may be represented by the following structural formula:
  • R represents hydrogen, halo having an atomic weight of about 19 to 36, and straight chain lower alkoxy, i.e., straight chain alkoxy having 1 to 4 carbon atoms, e.g., methoxy, ethoxy, isopropoxy or the like, and R and R each independently represent alkyl having 1 or 2 carbon atoms, i.e., methyl or ethyl.
  • the compounds of formula (1) above are known and may be prepared according to methods disclosed in the literature from known materials.
  • the present invention contemplates only the novel use of such compounds as anti-obesity and anti-diabetic agents.
  • the compounds of formula (I) are useful because they possess pharmacological activity in animals.
  • the compounds 'of formula (I) are useful as anti-obesity agents in the treatment of obesity as indicated by (l preventing an increase in the blood sugar level in male Wistar rats in groups of 4 which have fasted for 16 hours and then are given an initial dose of 200 milligrams per kilogram of animal body weight of the test compound orally. One hour later, the rats are given 2 grams per kilogram of animal body weight of maltose load. Fifteen minutes after administration of the maltose, the rats are anesthetized with 120 milligrams per kilogram of animal body weight of sodium hexobarbital after which blood is collected via cardiac puncture.
  • the blood samples are placed in an autoanalyzer cup containing 0.1 milliliters of heparin (1,000 units per milliliter).
  • the heparinized blood is used to determine the blood sugar level with an autoanalyzer.
  • the blood sugar content is compared to the control group which receives 0.5% carboxmethyl cellulose and are run concurrently, and by (2 preventing an increase in the blood sugar level in male Wistar rats in groups of 4 which are fasted for 16 hours and then are given an initial dose of 200 milligrams per kilogram of animal body weight of the test compound orally. One hour later, the rats are given 2.5 grams per kilogram of animal body weight of starch load.
  • the rats are anesthetized with 120 milligrams per kilogram of animal body weight of sodium hexobarbital after which blood is collected via cardiac puncture.
  • the blood samples are placed in an autoanalyzer cup'containing 0.1 milliliters of heparin (1,000 unitsper milliliter).
  • the heparinized blood is used to determine the blood sugar level with an autoanalyzer.
  • the blood sugar content is compared to the control group which receives 0.5% carboxmethyl cellulose and are run concurrently.
  • the blood sugar levels are calculated and compared to the control.
  • the compounds of formula (I) are also useful asjuvenile anti-diabetic agents in the treatment of diabetes in adults as indicated by the lowering of blood glucose in 6 to 8-week old male Royal Hart mice weighing 30 to 35 grams which are fasted in groups of 5 for 16 hours and then are given an initial dose of 200 milligrams per kilogram of animal body weight of the compound orally. One and one-half hours later, the mice are given orally 2 grams per kilogram of animal body weight of a glucose challenge. Twenty-five minutes later, the mice are anesthetized with milligrams per kilogram of animal body weight of sodium hexobarbital and 5 minutes later blood is collected via cardiac puncture.
  • the blood samples are placed in an autoanalyzer cup containing 0.025 milliliters of heparin 1,000 units per milliliter); and the samples are capped, shaken, and stored in ice.
  • the glucose content is determined by the autoanalyzer potassium ferric-cyanide N-2b method and are compared with a control group, which receives orally 0.5% carboxmethyl cellulose vehicle and are run concurrently.
  • the compounds of formula (I) may be administered orally or parenterally as such or admixed with conventional pharmaceutical carriers. They may be administered orally in such forms as tablets, dispersible powders, capsules, soft gelatin capsules, preferably soft gelatin capsules, and emulsions, and parenterally as emulsions, e.g., a sterile injectable emulsion.
  • the compositions for oral use may contain one or more conventional adjuvants, such as sweetening agents, flavoring agents, coloring agents and preserving agents, in order to provide an elegant and palatable preparation.
  • Tablets may contain the active ingredient in admixture with conventional pharmaceutically acceptable excipients, e.g., inert diluents, such as calcium carbonate, sodium carbonate, lactose, and talc, granulating and disintegrating agents, e.g., starch and alginic acid, binding agents, e.g., starch, gelatin and acacia, lubricating agents, e.g., magnesium stearate, stearic acid and talc, and absorbing agents such as colloidal silicone dioxide.
  • excipients e.g., inert diluents, such as calcium carbonate, sodium carbonate, lactose, and talc
  • granulating and disintegrating agents e.g., starch and alginic acid
  • binding agents e.g., starch, gelatin and acacia
  • lubricating agents e.g., magnesium stearate, stearic acid and talc
  • suspensions, and emulsions may contain the active ingredient in admixture with any of the conventional excipients utilized by the preparation of such compositions, e.g., suspending agents such as methylcellulose, tragacanth and sodium alginate; wetting agents such as lecithin, polyoxyethylene stearate and polyoxyethylene sorbitan monooleate, and preservatives such as ethyl-p-hydroxybenzoate.
  • suspending agents such as methylcellulose, tragacanth and sodium alginate
  • wetting agents such as lecithin, polyoxyethylene stearate and polyoxyethylene sorbitan monooleate
  • preservatives such as ethyl-p-hydroxybenzoate.
  • Capsules may contain the active ingredient admixed with an inert solid diluent. e.g., calcium carbonate, cal-.
  • Soft gelatin capsules may contain the active ingredient in admixture with conventional pharmaceutical 'excipients, e.g., inert carriers such as vegetable oils (soybean oil, corn oil and the like) polyethyleneglycol derivatives or mineral oils.
  • inert carriers such as vegetable oils (soybean oil, corn oil and the like) polyethyleneglycol derivatives or mineral oils.
  • the injectable compositions are formulated as known in the art. These pharmaceutical preparations may contain up to about 90% of the active ingredient in combination with the carrier or adjuvant.
  • the anti-obesity effective dosage of active ingredient employed for the treatment of obesity and the anti-diabetic effective amount of active ingredient employed in the treatment of diabetes may vary depending on the particular compound employed, the mode of administration and the severity of the condition being treated. However, in general, satisfactory results are obtained for both the hypolipodemia effect and the anti-diabetic effect when the compounds of formula (I) are administered at a daily dosage of from about 1 milligram to about 200 milligrams per kilogram of animal body weight, p.o., preferably given in divided doses two to four times a day, or in sustained release form. For most large mammals, the total daily dosage for both indications is from about 75 to about 1,500 milligrams. Dosage forms suitable for internal use comprise from about to about 750 milligrams of the active compound in intimate admixture with a solid or liquid pharmaceutically acceptable carrier or diluent.
  • a representative formulation suitable for oral administration is a tablet, capsule or soft gelatin capsule prepared by standard tabletting or encapsulating techniques which contains the following and may be administered 2 to 4 times a day in the treatment of obesity or diabetes.
  • Capsule p-pivaloyl toluene I00 tragacanth lactose 300 corn starch talcum magnesium stearate The following pharmaceutical compositions are formulated with the indicated amount of active agent using conventional techniques.
  • the injcctable cmulsion, the oral liquid suspension, and the oral liquid emulsion represent formulations useful as unit doses and may be administered in the treatment of obesity or diabetes.
  • the injectable emulsion is suitable for admin istration once or twice a day whereas the oral liquid suspension and the oral liquid emulsion is suitably administered 2 to 4 times per day for this purpose.
  • EXAMPLE 3 lngredient Weight (mgr) Oral liquid suspension p-pivaloyl toluene 100 magnesium aluminum silicate 47.5 flavor q s. color q.s methyl paraben. U.S.P. 4.5 propyl paraben. U.S.P. l.() polysorbate (e.g., Tween 80). U.S.P. 5 sorbitol solution, 707:. U.S.P. 2.500 buffer agent to adjust pH for desired stability q.s water q.s. to
  • EXAMPLE 4 Ingredient Weight (mg) Sterile inject- ()ral liquid able emulsion emulsion p-pivaloyl toluene 200 I00 sodium. carboxy methyleellulose. U.S.P. 12.5 polyvinylpyrrolidone 5 benzoyl alcohol 00] sodium chloride to be adjusted to an isotonic concentration flavor q.s. color q.s. methyl paraben. U.S.P. 4.5 propyl paraben. U.S.P. I.() polysorbate 80 (eg. Tween 80). U.S.P. l sorbitol solution. 2.500 70% U.S.P. buffer agent to adjust pH for desired stability qs qis. water for injection q.s. to
  • compositions from the standpoint of preparation and ease of administration are soft gelatin capsules containing from about to 200 milligrams of the active ingredient.
  • R represents hydrogen, halo having an atomic from about 20 milligrams to about 750 milligrams per weight of about 19 to 36, or straight chain lower unit dosage. alkoxy, and 6.
  • a pharmaceutical composition useful as an anti- R. and R each independently represent lk l h i obesity agent comprising a compound of the formula:

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Certain substituted or unsubstituted p-alkanoyl toluenes, e.g., p-alkanoyl toluene, are useful as anti-obesity and anti-diabetic agents.

Description

United States Patent H0 et al.
Dec. 2, 1975 SUBSTITUTED OR UNSUBSTITUTED P-ALKANOYL TOLUENES AS ANTI-OBESlTY AND ANTI-DIABETIC AGENTS Inventors: Robert S. H0, Denville; William J.
Houlihan, Mountain Lakes; Jeffrey Nadelson, Lake Parsippany, all of Assignee: Sandoz lnc., East Hanover, NJ.
Filed: Feb. 3, 1975 Appl. No.: 546,756
Related US. Application Data Continuation-impart of Ser. No. 445,265, Feb. 25, 1974. abandoned. v
US. Cl. 424/331 Int. Cl. A61K 31/12 Field of Search 424/331 [56 References Cited Primary Examiner-Norman A. Drezin Attorney, Agent, or Firm-Gerald D. Sharkin; Robert S. Honor [57,] ABSTRACT Certain substituted or unsubstituted p-alkanoyl toluenes, e.g., p-alkanoyl toluene, are useful as antiobesity and anti-diabetic agents.
8 Claims, N0 Drawings SUBSTITUTED OR UNSUBSTITUTED P-ALKANOYL TOLUENES AS ANTI-OBESITY AND ANTI-DIABETIC AGENTS This application is a continuation-in-part of copending application Ser. No. 445,265, filed Feb. 25, 1974,
now abandoned.
This invention relates to the pharmaceutical activity of p-alkanoyl toluenes. More particularly, this invention concerns the use of substituted or unsubstituted palkanoyl toluenes in the treatment of obesity and diabetes. The invention also relates to pharmaceutical compositions containing these compounds as an active ingredient thereof.
The active agents with which this invention is conccrned may be represented by the following structural formula:
where R represents hydrogen, halo having an atomic weight of about 19 to 36, and straight chain lower alkoxy, i.e., straight chain alkoxy having 1 to 4 carbon atoms, e.g., methoxy, ethoxy, isopropoxy or the like, and R and R each independently represent alkyl having 1 or 2 carbon atoms, i.e., methyl or ethyl.
The compounds of formula (1) above are known and may be prepared according to methods disclosed in the literature from known materials. The present invention contemplates only the novel use of such compounds as anti-obesity and anti-diabetic agents.
The compounds of formula (I) are useful because they possess pharmacological activity in animals. In particular, the compounds 'of formula (I) are useful as anti-obesity agents in the treatment of obesity as indicated by (l preventing an increase in the blood sugar level in male Wistar rats in groups of 4 which have fasted for 16 hours and then are given an initial dose of 200 milligrams per kilogram of animal body weight of the test compound orally. One hour later, the rats are given 2 grams per kilogram of animal body weight of maltose load. Fifteen minutes after administration of the maltose, the rats are anesthetized with 120 milligrams per kilogram of animal body weight of sodium hexobarbital after which blood is collected via cardiac puncture. The blood samples are placed in an autoanalyzer cup containing 0.1 milliliters of heparin (1,000 units per milliliter). The heparinized blood is used to determine the blood sugar level with an autoanalyzer. The blood sugar content is compared to the control group which receives 0.5% carboxmethyl cellulose and are run concurrently, and by (2 preventing an increase in the blood sugar level in male Wistar rats in groups of 4 which are fasted for 16 hours and then are given an initial dose of 200 milligrams per kilogram of animal body weight of the test compound orally. One hour later, the rats are given 2.5 grams per kilogram of animal body weight of starch load. 'Thirty minutes after administration of the starch, the rats are anesthetized with 120 milligrams per kilogram of animal body weight of sodium hexobarbital after which blood is collected via cardiac puncture. The blood samples are placed in an autoanalyzer cup'containing 0.1 milliliters of heparin (1,000 unitsper milliliter). The heparinized blood is used to determine the blood sugar level with an autoanalyzer. The blood sugar content is compared to the control group which receives 0.5% carboxmethyl cellulose and are run concurrently. The blood sugar levels are calculated and compared to the control.
The compounds of formula (I) are also useful asjuvenile anti-diabetic agents in the treatment of diabetes in adults as indicated by the lowering of blood glucose in 6 to 8-week old male Royal Hart mice weighing 30 to 35 grams which are fasted in groups of 5 for 16 hours and then are given an initial dose of 200 milligrams per kilogram of animal body weight of the compound orally. One and one-half hours later, the mice are given orally 2 grams per kilogram of animal body weight of a glucose challenge. Twenty-five minutes later, the mice are anesthetized with milligrams per kilogram of animal body weight of sodium hexobarbital and 5 minutes later blood is collected via cardiac puncture. The blood samples are placed in an autoanalyzer cup containing 0.025 milliliters of heparin 1,000 units per milliliter); and the samples are capped, shaken, and stored in ice. The glucose content is determined by the autoanalyzer potassium ferric-cyanide N-2b method and are compared with a control group, which receives orally 0.5% carboxmethyl cellulose vehicle and are run concurrently.
For such'uses, the compounds of formula (I) may be administered orally or parenterally as such or admixed with conventional pharmaceutical carriers. They may be administered orally in such forms as tablets, dispersible powders, capsules, soft gelatin capsules, preferably soft gelatin capsules, and emulsions, and parenterally as emulsions, e.g., a sterile injectable emulsion. The compositions for oral use may contain one or more conventional adjuvants, such as sweetening agents, flavoring agents, coloring agents and preserving agents, in order to provide an elegant and palatable preparation. Tablets may contain the active ingredient in admixture with conventional pharmaceutically acceptable excipients, e.g., inert diluents, such as calcium carbonate, sodium carbonate, lactose, and talc, granulating and disintegrating agents, e.g., starch and alginic acid, binding agents, e.g., starch, gelatin and acacia, lubricating agents, e.g., magnesium stearate, stearic acid and talc, and absorbing agents such as colloidal silicone dioxide. The tablets may be uncoated or coated by known techniques to delay disintegration and absorption in the gastro-intestinal tract and thereby provide a sustained action over a longer period. Similarly, suspensions, and emulsions may contain the active ingredient in admixture with any of the conventional excipients utilized by the preparation of such compositions, e.g., suspending agents such as methylcellulose, tragacanth and sodium alginate; wetting agents such as lecithin, polyoxyethylene stearate and polyoxyethylene sorbitan monooleate, and preservatives such as ethyl-p-hydroxybenzoate. Capsules may contain the active ingredient admixed with an inert solid diluent. e.g., calcium carbonate, cal-.
cium phosphate and kaolin. Soft gelatin capsules may contain the active ingredient in admixture with conventional pharmaceutical 'excipients, e.g., inert carriers such as vegetable oils (soybean oil, corn oil and the like) polyethyleneglycol derivatives or mineral oils. The injectable compositions are formulated as known in the art. These pharmaceutical preparations may contain up to about 90% of the active ingredient in combination with the carrier or adjuvant.
The anti-obesity effective dosage of active ingredient employed for the treatment of obesity and the anti-diabetic effective amount of active ingredient employed in the treatment of diabetes may vary depending on the particular compound employed, the mode of administration and the severity of the condition being treated. However, in general, satisfactory results are obtained for both the hypolipodemia effect and the anti-diabetic effect when the compounds of formula (I) are administered at a daily dosage of from about 1 milligram to about 200 milligrams per kilogram of animal body weight, p.o., preferably given in divided doses two to four times a day, or in sustained release form. For most large mammals, the total daily dosage for both indications is from about 75 to about 1,500 milligrams. Dosage forms suitable for internal use comprise from about to about 750 milligrams of the active compound in intimate admixture with a solid or liquid pharmaceutically acceptable carrier or diluent.
Compounds of formula (I) which can be used as the active ingredient include the following:
a. 2-ehloro-4-pivaloyl toluene b. 2-methoxy-4-pivaloyl toluene, or
c. p-pivaloyl toluene, the latter being especially preferred.
A representative formulation suitable for oral administration is a tablet, capsule or soft gelatin capsule prepared by standard tabletting or encapsulating techniques which contains the following and may be administered 2 to 4 times a day in the treatment of obesity or diabetes.
EXAMPLE 1 Ingredient Weight tmg.)
Capsule p-pivaloyl toluene I00 tragacanth lactose 300 corn starch talcum magnesium stearate The following pharmaceutical compositions are formulated with the indicated amount of active agent using conventional techniques. The injcctable cmulsion, the oral liquid suspension, and the oral liquid emulsion represent formulations useful as unit doses and may be administered in the treatment of obesity or diabetes. The injectable emulsion is suitable for admin istration once or twice a day whereas the oral liquid suspension and the oral liquid emulsion is suitably administered 2 to 4 times per day for this purpose.
EXAMPLE 3 lngredient Weight (mgr) Oral liquid suspension p-pivaloyl toluene 100 magnesium aluminum silicate 47.5 flavor q s. color q.s methyl paraben. U.S.P. 4.5 propyl paraben. U.S.P. l.() polysorbate (e.g., Tween 80). U.S.P. 5 sorbitol solution, 707:. U.S.P. 2.500 buffer agent to adjust pH for desired stability q.s water q.s. to
EXAMPLE 4 Ingredient Weight (mg) Sterile inject- ()ral liquid able emulsion emulsion p-pivaloyl toluene 200 I00 sodium. carboxy methyleellulose. U.S.P. 12.5 polyvinylpyrrolidone 5 benzoyl alcohol 00] sodium chloride to be adjusted to an isotonic concentration flavor q.s. color q.s. methyl paraben. U.S.P. 4.5 propyl paraben. U.S.P. I.() polysorbate 80 (eg. Tween 80). U.S.P. l sorbitol solution. 2.500 70% U.S.P. buffer agent to adjust pH for desired stability qs qis. water for injection q.s. to
q.s. to 1 ml. 5 ml.
The preferred pharmaceutical compositions from the standpoint of preparation and ease of administration are soft gelatin capsules containing from about to 200 milligrams of the active ingredient.
What is claimed is:
1. A method for treating obesity which comprises administering to a mammal in need of said treatment an anti-obesity effective amount of a compound of the formula:
where 3,9 24,003 R represents hydrogen, halo having an atomic from about 20 milligrams to about 750 milligrams per weight of about 19 to 36, or straight chain lower unit dosage. alkoxy, and 6. A pharmaceutical composition useful as an anti- R. and R each independently represent lk l h i obesity agent comprising a compound of the formula:
1 to 2 carbon atoms. 5
2. The method of claim 1 in which the compound is: CH
(H RI R. cl o HRC i R at C where R R and R are as defined in claim 1, and a CH. pharmaceutically acceptable carrier therefor. said compound being present in an amount of from about i 75 milligrams to about 1500 milligrams. The methQd of Clam 1 m Whlch the Compound 15 7. The composition of claim 6 in which the active in- P'P toluenegredient is p-pivaloyl toluene.
4. The method of claim 1 wherein the compound is 7 8, Th pharmaceutical composition f laim 6 administered orally at a daily dosage of from about 75 wherein said active ingredient is present in said compomilligrams to about 1500 milligrams. sition in an amount of from about milligrams to 5. The method of claim 1 wherein the compound is about 750 milligrams per unit dosage. orally administered in a unit dosage form comprising 3 ,924 ,003 Dec. 2, 1975 Patent No. Dated Invent Robert 8. Ho, William J. Houlihan, Jeffrey Nadelson It is certified that error appears in the above-identified patent and that said Letters Patent are hereby corrected as shown below:
Col. 3, line 16, please delete the word 'hypolipodemia" and insert in its place the word anti-obesity Signed and Scaled this Sixth Day of December I977 [SEAL] Attest:
RUTH C. MASON LUTRELLE F. PARKER Attesting Officer Acting Commissioner of Patents and Trademarks

Claims (8)

1. A METHOD FOR TREATING OBESITY WHICH COMPRISES ADMINISTERING TO A MAMMAL IN NEED OF SAID TREATMENT AN ANTI-OBESITY EFFECTIVE AMOUNT OF A COMPOUND OF THE FORMULA:
2. The method of claim 1 in which the compound is:
3. The method of claim 1 in which the compound is p-pivaloyl toluene.
4. The method of claim 1 wherein the compound is administered orally at a daily dosage of from about 75 milligrams to about 1500 milligrams.
5. The method of claim 1 wherein the compound is orally administered in a unit dosage form comprising from about 20 milligrams to about 750 milligrams per unit dosage.
6. A pharmaceutical composition useful as an anti-obesity agent comprising a compound of the formula:
7. The composition of claim 6 in which the active ingredient is p-pivaloyl toluene.
8. The pharmaceutical composition of claim 6 wherein said active ingredient is present in said composition in an amount of from about 20 milligrams to about 750 milligrams per unit dosage.
US546756A 1974-02-25 1975-02-03 Substituted or unsubstituted p-alkanoyl toluenes as anti-obesity and anti-diabetic agents Expired - Lifetime US3924003A (en)

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US546756A US3924003A (en) 1974-02-25 1975-02-03 Substituted or unsubstituted p-alkanoyl toluenes as anti-obesity and anti-diabetic agents
US05/605,973 US3968247A (en) 1974-02-25 1975-08-20 Substituted or unsubstituted p-alkanoyl toluenes as anti-diabetic agents

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US44526574A 1974-02-25 1974-02-25
US546756A US3924003A (en) 1974-02-25 1975-02-03 Substituted or unsubstituted p-alkanoyl toluenes as anti-obesity and anti-diabetic agents

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4015010A (en) * 1975-03-03 1977-03-29 Sandoz, Inc. Alkanoyl substituted benzoic acids and esters
US7608578B2 (en) 2000-08-11 2009-10-27 Temple University - Of The Commonwealth System Of Higher Education Obesity controlling method
US7737109B2 (en) 2000-08-11 2010-06-15 Temple University Of The Commonwealth System Of Higher Education Obesity controlling method

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
Landrum et al., Chemical Abstracts 48:13655c (1954). *
Landrum et al., Chemical Abstracts 49:15791g (1955). *
Pearson et al., Chemical Abstracts 50:4070b (1956). *
Ropp et al., Chemical Abstracts 53:6174c (1959). *
Tsatsas, Chemical Abstracts 74:42099x (1971). *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4015010A (en) * 1975-03-03 1977-03-29 Sandoz, Inc. Alkanoyl substituted benzoic acids and esters
US7608578B2 (en) 2000-08-11 2009-10-27 Temple University - Of The Commonwealth System Of Higher Education Obesity controlling method
US7737109B2 (en) 2000-08-11 2010-06-15 Temple University Of The Commonwealth System Of Higher Education Obesity controlling method

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