USRE30910E - Reducing cholesterol levels - Google Patents
Reducing cholesterol levels Download PDFInfo
- Publication number
- USRE30910E USRE30910E US06/117,239 US11723980A USRE30910E US RE30910 E USRE30910 E US RE30910E US 11723980 A US11723980 A US 11723980A US RE30910 E USRE30910 E US RE30910E
- Authority
- US
- United States
- Prior art keywords
- compound
- cholesterol
- human
- dihydroxy
- administered
- 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, expires
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
- C07J9/005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane containing a carboxylic function directly attached or attached by a chain containing only carbon atoms to the cyclopenta[a]hydrophenanthrene skeleton
-
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/575—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0055—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives
- C07J41/0061—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives one of the carbon atoms being part of an amide group
Definitions
- This invention relates to and has as its objective a method of reducing the levels of cholesterol and other lipids, especially triglycerides, in mammals.
- Current medical theory holds that there is a causal relationship between elevated cholesterol and lipid levels and the development of artherosclerosis and other adverse conditions in mammals.
- Artherosclerotic conditions are a major cause of death by virtue of their relation to hardening and narrowing of blood vessel walls and the occurrence of thromboses leading to coronary attacks and strokes.
- the rate limiting step in the synthesis of cholesterol in the body may be the conversion of 3 ⁇ -hydroxy-3 ⁇ -methyl glutaric acid to mevalonic acid.
- This reaction seems to be controlled by the activity of a catalytic enzyme, 3 ⁇ -hydroxy 3 ⁇ -methyl glutaryl CoA reductase. Therefore, by controlling the activity of this enzyme, the synthesis of cholesterol is controlled.
- the synthesis of cholesterol in the body it is possible to reverse the mechanism whereby the body distributes and causes the deposit of excess cholesterol in various body pools, such as the gall bladder and blood vessels. Inhibiting or suppressing synthesis cholesterol, causes the body to deplete or withdraw from the various body pools, wherein excess cholesterol was previously deposited, the excess cholesterol therein deposited.
- the suppression of cholesterol synthesis will result in the overall reduction of cholesterol and other lipid levels in the body.
- the suppression of the synthesis of cholesterol will result in a reversal of the mechanism by which excess cholesterol was previously deposited in the various body pools and therefore will result in a lowering of the cholesterol and lipid levels in mammals.
- a method to reduce the cholesterol and lipid, including triglyceride, levels of mammals which comprises administering to said mammals an effective amount of a composition selected from the group consisting of those of the formula: ##STR2## wherein R is selected from the group consisting of OH, NHCH 2 COOH and NHCH 2 CH 2 SO 3 H; each X is hydrogen; each Y is selected from the group consisting of hydroxy and acyloxy; and when taken together, X and Y is oxo (O ⁇ ).
- the compounds of this invention may be administered in the form of their non-toxic pharmaceutically acceptable salts, for example, the alkaline metal salts, such as the sodium or potassium salts thereof.
- administration of the compounds of Formula I of this invention to hypercholesteremic mammals results in the inhibition of activity of the rate limiting enzyme which controls the rate of cholesterol synthesis in mammals, and thus results in a lowering of the cholesterol and other lipid levels of the hypercholesteremic mammal being treated.
- the inhibition of cholesterol synthesis by the practice of this invention results in a decrease of the natural distribution of cholesterol into the plasma and bile of the mammal being treated, and consequently will lead to a reversal of the process whereby excessive cholesterol has been previously deposited resulting in the formation of cholesterol gall stones and artherosclerotic plaque.
- administration of the compounds of Formula I, in the practice of this invention, to hypercholesteremic mammals will apparently lead to a depletion of excessive cholesterol deposits in the body of said mammal, for example, cholesterol gall stones and artherosclerotic plaque.
- the preferred acyloxy radicals are those of hydrocarbon carboxylic acids of less than twelve carbon atoms, as exemplified by the lower alkanoic acids (e.g., acetic, propionic, and butyric acids), the lower alkenoic acids, the monocyclic aryl carboxylic acids (e.g., benzoic and toluic acids), the monocyclic aryl lower alkanoic acids (e.g., phenacetic and-B-phenylpropionic acids), the cycloalkane carboxylic acids and the cycloalkene carboxylic acids.
- the lower alkanoic acids e.g., acetic, propionic, and butyric acids
- the lower alkenoic acids e.g., benzoic and toluic acids
- the monocyclic aryl lower alkanoic acids e.g., phenacetic and-B-phenylpropionic acids
- the cycloalkane carboxylic acids
- compositions of this invention may be administered to the patients being treated in accordance with the method of this invention. It has been found that satisfactory results are obtained when the compositions of this invention are orally administered to the patient in a daily amount of from about 50 milligrams to about 1.5 grams. Best results appear to be obtained when the initial dosage is in the range of from about 0.5-1.5 gm. per day and then gradually reduced and maintained at a level of about 100 mg. per day depending upon the patient being treated and the results obtained.
- the active substances of Formula I hereof may be incorporated in such suitable final dosage forms as may be satisfactorily prepared and employed by the worker skilled in the art.
- the commonly employed, pharmaceutically acceptable dosage forms suitable for oral administration containing the active substance of Formula I in sufficient concentration to attain the desired results may be utilized.
- the pharmaceutically acceptable, non-toxic inert carriers usually employed for such purposes may be utilized to prepare such dosage forms as tablets, capsules, elixirs, solutions, suspensions and the like. Most preferably, satisfactory results have been obtained by the use of tablets or capsules containing the active ingredient in a concentration of from about 50 to 500 mg., although other concentrations have also provided satisfactory results.
- the invention may be further illustrated by the following Examples.
- Final orally administerable dosage forms incorporating the amounts of active substances set forth in Table A were prepared and administered on a daily basis to patients having abnormally elevated lipid, for example cholesterol and triglyceride, levels. These materials were administered to the patients over an extended period of time during which there was a substantial reduction in the lipid, i.e., cholesterol and triglyceride, levels of the patients, to within normal ranges.
- lipid for example cholesterol and triglyceride
- Bile acids i.e., sodium taurocholate, sodium taurochenodeoxycholate and sodium taurodeoxycholate, were added to the stock diets at a level of 1%.
- the experimental diets were fed for one week after which the bile ducts of the test animals were cannulated and their bile collected for a period of 30 to 60 minutes. At the end of the bile collection period, the test animals were sacrificed, their livers removed and a microsomal fraction was prepared by ultracentrifugation.
- TCDC chenodeoxycholic acid
- 3 ⁇ ,7 ⁇ -dihydroxy-5 ⁇ -cholanic acid was orally administered to the patient.
- the daily dosage level of 3 ⁇ ,7 ⁇ -dihydroxy-5 ⁇ -cholanic acid was 750 mg., administered three times per day in capsule form, each containing 250 mg. of the compound.
- the lipid values of the patient were found to be:
- Two patients with elevated cholesterol level and cholelithiasis were treated with a compound of the instant invention to determine its effect in lowering the cholesterol level of the patients.
- the patient E. Y. experienced a 70% reduction in the size of the cholesterol stones in the gall bladder (confirmed by radiological studies), without a concommitant rise in the patient's overall cholesterol level.
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
Abstract
Description
TABLE A ______________________________________ Material Amount ______________________________________ 3α,7α-dihydroxy-5β-cholanic acid 250 mg. 12-desoxy-cholytaurine 250 mg. 3α,7α-diacetoxy-5β-cholanic acid 250 mg. 12-desoxy-cholylglycine 250 mg. 3,7-dioxy-5β-cholanic acid 250 mg. 3α,7β-dihydroxy-5β-cholanic acid 250 mg. ______________________________________
______________________________________ Enzyme Liver Test No. Activity** Cholesterol*** Compound Animals HMG C-7H Concentration ______________________________________ Stock Diet 6 93.9 9.11 2.45 (SD) SD + 1% TCDC 6 35.1 8.49 2.57 SD + 1% TDC 4 63.8 7.22 3.78 SD + 1% TC 6 36.6 3.08 6.09 ______________________________________ *TCDC = taurochenodeoxycholic acid TDC = taurodeoxycholic acid TC = taurocholic acid **HMG = HMG CoA reductase C7H = cholesterol 7hydroxylase Activity is given in pmoles/mg protein/min ***mg/g (wet wt.)
______________________________________ Cholesterol: 250 ± 7 mg/100 ml Triglycerides: 2021 ± 326 mg/100 ml ______________________________________
______________________________________ Cholesterol: 190 ± 18 mg/100 ml Triglycerides: 1484 ± 308 mg/100 ml ______________________________________
TABLE B ______________________________________ Cholesterol Values After Patient Dosage Control 1 Mo. 3 Mo. 4 Mo. 6 Mo. ______________________________________ N. C. 750 mg/day 262 246 207 -- -- R. R. " 271 -- -- 173 -- C. F. " 305 -- -- 266 -- K. S. " 230 -- -- 107 -- G. W. " 450 -- -- -- 358 ______________________________________
TABLE C ______________________________________ Cholesterol Values After Patient Test Compound Control 3 Mo. 7 Mo. 12 Mo. ______________________________________ E. Y. 3α,7α-dihydroxy- 5β-cholanic acid 243 258 -- 244 T. S. 3α,7α-dihydroxy- 5β-cholanic acid 279 -- 235 -- ______________________________________
Claims (11)
- and the non-toxic, pharmaceutically acceptable salts thereof..]. .[.2. The method of claim 1, wherein the compound is 3α,7α-dihydroxy-5β-cholanic acid..]. .[.3. The method of claim 1, wherein in the compound is administered in a daily dosage amount of about 750 mg. per day..]. .[.4. The method of claim 1, wherein in the
- compound each Y is hydroxy..]. .[.5. The method of claim 1, wherein the compound is 3α,7β-dihydroxy-5β-cholanic acid..]. .[.6. The method of reducing the cholesterol levels of human beings, which comprises;a. orally administering over an extended period of time, to a human being in a hypercholesteremic state;b. a small but effective amount sufficient to effect a reduction in the cholesterol level of said human being, of a compound of the formula: ##STR4## whereinR is OH, NHCH2 COOH, or NHCH2 CH2 SO3 H;each X is hydrogen;each Y is hydroxy or acyloxy; and X and Y when taken together is oxo (O═);
- and the non-toxic, pharmaceutically acceptable salts thereof..]. .[.7. The method of claim 6, wherein the compound is 3α,7α-dihydroxy-5β-cholanic acid..]. .[.8. The method of claim 6 wherein the compound is administered in a daily dosage amount of 750 mg. per day..]. .[.9. The method of claim 5, wherein the hypercholesteremic state of the human being is hypercholesterolemia..].
- .[.0. The method of claim 6, wherein the compound, each Y is hydroxy..]. .[.11. The method of claim 6, wherein the compound is 3α,7β-dihydroxy-5β-cholanic acid..]. .[.12. The method of reducing the triglyceride levels of human beings, which comprises;a. orally administering over an extended period of time, to a human being in a hypertriglyceridemic state;b. a small but effective amount sufficient to effect a reduction of the triglyceride level of said human being, of a compound of the formula: ##STR5## wherein R is OH, NHCH2 COOH, or NHCH2 CH2 SO3 H;each X is hydrogen;each Y is hydroxy, or acyloxy, andX and Y when taken together is oxo (O═); and the non-toxic,
- pharmaceutically acceptable salts thereof..]. .[.13. The method of claim 12, wherein the compound is 3α,7α-dihydroxy-5β-cholanic
- acid..]. .[.14. The method of claim 12, wherein the compound is administered in a daily dosage amount of about 750 mg. per day..]. .[.15. The method of claim 12, wherein in the compound, each Y is hydroxy..]. .[.16. The method of claim 12, wherein the compound is
- 3α,7β-dihydroxy-5β-cholanic acid..]. 17. The method of reducing cholesterol levels of human beings, which comprises;a. Orally administering over an extended period of time, to a human being suffering from cholelithiasis;b. A small but effective amount sufficient to effect a reduction in the cholesterol level of said human being, of a compound of the formula: ##STR6## wherein R is OH, NHCH2 COOH or NHCH2 CH2 SO3 H; each X is hydrogen;each Y is hydroxy or acyloxy; andX and Y when taken together is oxo (O═); and the non-toxic
- pharmaceutically acceptable salts thereof. .[.18. The method of claim 17, wherein the compound is 3α,7α-dihydroxy-5β-cholanic acid..]. .[.19. The method of claim 17, wherein the compound is
- 3α,7β-dihydroxy-5β-cholanic acid..]. .Iadd.20. The method of claim 17 wherein the compound is administered in a daily dosage amout
- of from about 0.5 to 1.5 grams per day. .Iaddend. .Iadd.21. The method of reducing cholesterol levels of human beings, which comprises:a. Orally administering over an extended period of time, to a human being suffering from cholelithiasis;b. A small but effective amount sufficient to effect a reduction in the cholesterol level of said human being, of the compound 3α,7β-dihydroxy-5β-cholanic acid, and the non-toxic
- pharmaceutically acceptable salts thereof. .Iaddend. .Iadd.22. The method of claim 21 wherein the compound is administered in a daily dosage amount of about 750 milligrams per day. .Iaddend. .Iadd.23. The method of claim 17 wherein the compound is administered in a daily dosage amount of about 500 to 750 milligrams per day. .Iaddend. .Iadd.24. The method of claim 17 wherein the compound is administered in a daily dosage amount of about 750 milligrams per day. .Iaddend. .Iadd.25. The method of claim 21 wherein the compound is administered in a daily dosage amount of from about 0.5 to 1.5 grams per day. .Iaddend. .Iadd.26. The method of claim 21 wherein the compound is administered in a daily dosage amount of about 500 to 750 milligrams per day. .Iaddend.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12629671A | 1971-03-19 | 1971-03-19 | |
US25906272A | 1972-06-02 | 1972-06-02 | |
US346751A US3859437A (en) | 1972-06-02 | 1973-04-02 | Reducing cholesterol levels |
US86732278A | 1978-01-05 | 1978-01-05 |
Related Parent Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US346751A Reissue US3859437A (en) | 1971-03-19 | 1973-04-02 | Reducing cholesterol levels |
US86732278A Continuation | 1971-03-19 | 1978-01-05 |
Publications (1)
Publication Number | Publication Date |
---|---|
USRE30910E true USRE30910E (en) | 1982-04-20 |
Family
ID=27494640
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US06/117,239 Expired - Lifetime USRE30910E (en) | 1971-03-19 | 1980-01-31 | Reducing cholesterol levels |
Country Status (1)
Country | Link |
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US (1) | USRE30910E (en) |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5234697A (en) * | 1992-06-22 | 1993-08-10 | Digestive Care Inc. | Compositions of gastric acid-resistant microspheres containing salts of bile acids |
US5260074A (en) * | 1992-06-22 | 1993-11-09 | Digestive Care Inc. | Compositions of digestive enzymes and salts of bile acids and process for preparation thereof |
US5262172A (en) * | 1992-06-19 | 1993-11-16 | Digestive Care Inc. | Compositions of gastric acid-resistant microspheres containing buffered bile acids |
US5302400A (en) * | 1992-06-22 | 1994-04-12 | Digestive Care Inc. | Preparation of gastric acid-resistant microspheres containing digestive enzymes and buffered-bile acids |
US5352682A (en) * | 1993-03-08 | 1994-10-04 | Digestive Care Inc. | Compositions containing salts of bile acid-aminosalicylate conjugates |
US5415872A (en) * | 1992-06-22 | 1995-05-16 | Digestive Care Inc. | Compositions of gastric acid-resistant microspheres containing salts of bile acids |
US5460812A (en) * | 1992-06-22 | 1995-10-24 | Digestive Care Inc. | Compositions of digestive enzymes and salts of bile acids and process for preparation thereof |
US5578304A (en) * | 1992-06-22 | 1996-11-26 | Digestive Care Inc. | Compositions of digestive enzymes and salts of bile acids and process for preparation thereof |
US5674488A (en) * | 1994-10-07 | 1997-10-07 | Reich; John J. | Method for prevention and treatment of hyperchlolesterolemia by in vivo hydrogenation of cholesterol |
US5750104A (en) * | 1996-05-29 | 1998-05-12 | Digestive Care Inc. | High buffer-containing enteric coating digestive enzyme bile acid compositions and method of treating digestive disorders therewith |
US20070078115A1 (en) * | 1998-11-26 | 2007-04-05 | Burdick David C | Phytosterol and/or phytostanol derivatives |
-
1980
- 1980-01-31 US US06/117,239 patent/USRE30910E/en not_active Expired - Lifetime
Non-Patent Citations (51)
Title |
---|
Admirand et al., "The Physiochemical Basis of Cholesterol Gallstone Formation in Man", J. Clin. Invest. 47, 1043-1052, (1968). |
Angelin et al., (Abstract) 6th Int'l. Symposium on Drugs Affecting Lipid Metabolism (1977). |
Bateson et al., (Abstract) Ibid. |
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Bateson, Lancet, Oct. 30, 1976, pp. 962-963. |
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Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5262172A (en) * | 1992-06-19 | 1993-11-16 | Digestive Care Inc. | Compositions of gastric acid-resistant microspheres containing buffered bile acids |
US5405621A (en) * | 1992-06-19 | 1995-04-11 | Digestive Care Inc. | Compositions of gastric acid-resistant microspheres containing buffered bile acids |
US5302400A (en) * | 1992-06-22 | 1994-04-12 | Digestive Care Inc. | Preparation of gastric acid-resistant microspheres containing digestive enzymes and buffered-bile acids |
US5234697A (en) * | 1992-06-22 | 1993-08-10 | Digestive Care Inc. | Compositions of gastric acid-resistant microspheres containing salts of bile acids |
US5324514A (en) * | 1992-06-22 | 1994-06-28 | Digestive Care Inc. | Compositions of digestive enzymes and salts of bile acids and process for preparation thereof |
US5260074A (en) * | 1992-06-22 | 1993-11-09 | Digestive Care Inc. | Compositions of digestive enzymes and salts of bile acids and process for preparation thereof |
US5415872A (en) * | 1992-06-22 | 1995-05-16 | Digestive Care Inc. | Compositions of gastric acid-resistant microspheres containing salts of bile acids |
US5460812A (en) * | 1992-06-22 | 1995-10-24 | Digestive Care Inc. | Compositions of digestive enzymes and salts of bile acids and process for preparation thereof |
US5578304A (en) * | 1992-06-22 | 1996-11-26 | Digestive Care Inc. | Compositions of digestive enzymes and salts of bile acids and process for preparation thereof |
US5352682A (en) * | 1993-03-08 | 1994-10-04 | Digestive Care Inc. | Compositions containing salts of bile acid-aminosalicylate conjugates |
US5674488A (en) * | 1994-10-07 | 1997-10-07 | Reich; John J. | Method for prevention and treatment of hyperchlolesterolemia by in vivo hydrogenation of cholesterol |
US5750104A (en) * | 1996-05-29 | 1998-05-12 | Digestive Care Inc. | High buffer-containing enteric coating digestive enzyme bile acid compositions and method of treating digestive disorders therewith |
US20070078115A1 (en) * | 1998-11-26 | 2007-04-05 | Burdick David C | Phytosterol and/or phytostanol derivatives |
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