US3839565A - Chemical process - Google Patents
Chemical process Download PDFInfo
- Publication number
- US3839565A US3839565A US00302508A US30250872A US3839565A US 3839565 A US3839565 A US 3839565A US 00302508 A US00302508 A US 00302508A US 30250872 A US30250872 A US 30250872A US 3839565 A US3839565 A US 3839565A
- Authority
- US
- United States
- Prior art keywords
- hydroxy
- acyloxy
- alkoxy
- group
- chol
- 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
- 238000001311 chemical methods and process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims abstract description 14
- 241000124008 Mammalia Species 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 9
- 150000002632 lipids Chemical class 0.000 claims abstract description 7
- 235000012000 cholesterol Nutrition 0.000 claims abstract description 6
- 230000000260 hypercholesteremic effect Effects 0.000 claims abstract description 6
- -1 HYDROCARBON CARBOXYLIC ACID Chemical class 0.000 abstract description 11
- 231100000252 nontoxic Toxicity 0.000 abstract description 10
- 230000003000 nontoxic effect Effects 0.000 abstract description 10
- 150000003839 salts Chemical class 0.000 abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 8
- 239000001257 hydrogen Substances 0.000 abstract description 8
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 abstract description 8
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 5
- 229930195733 hydrocarbon Natural products 0.000 abstract description 5
- 229960003080 taurine Drugs 0.000 abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical class [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 2
- DHMQDGOQFOQNFH-CNRUNOGKSA-N 2-amino-2-tritioacetic acid Chemical group [3H]C(N)C(O)=O DHMQDGOQFOQNFH-CNRUNOGKSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 17
- 239000002253 acid Substances 0.000 description 13
- 239000000203 mixture Substances 0.000 description 10
- 125000004423 acyloxy group Chemical group 0.000 description 9
- 125000003545 alkoxy group Chemical group 0.000 description 8
- 201000001883 cholelithiasis Diseases 0.000 description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000008194 pharmaceutical composition Substances 0.000 description 5
- 239000004471 Glycine Substances 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 208000035150 Hypercholesterolemia Diseases 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 3
- 208000031226 Hyperlipidaemia Diseases 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 208000001130 gallstones Diseases 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 208000006575 hypertriglyceridemia Diseases 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
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
Definitions
- R is selected from the group consisting of an amino acid, for example glycine or turine, hydroxy, acyloxy or alkoxy; and each X is hydrogen; and each Y is hydroxy, acyloxy or alkoxy; and when taken together, X and Y is oxo (0:); and the non-toxic, pharmaceutically acceptable salts thereof.
- compositions of this invention have been found to be effective may be included such conditions as hypercholesterolemia, hypertriglyceridemia and cholelithiasis, among others. It has been found that most satisfactory results are obtained when a patient suffering from cholelithiasis, i.e. cholesterol gallstones, is treated with the compositions of this invention. In these cases, it has been discovered that after relatively short periods of treatment with the compositions of this invention, the patients gallstones begin to rapidly dissolve, without the need for surgery.
- the preferred compounds of this invention are those of Formula L wherein Y and R are hydroxy, although the other compounds also provide satisfactory results.
- specific compounds which may be employed in the practice of this invention may be included such compounds as, 3a,7a dihydroxy 5fi-chol-l1-en-24-oic acid, 3a,7a-diacyloxy-5/3-chol-l1-en-24-oic acid, for example, 30:,70: diacetoxy-SB-chol-l1-en-24-oic acid, 3,7-dioxy-5B- chol-11-en-24-oic acid, 3oz acyloxy-7a-hydroxy-5fi-chol- 11-en-24-oic acid, and other like compounds.
- non-toxic, pharmaceutically acceptable salts which may be employed in the practice of this invention include such salts as the alkali metal salts of the compounds of Formula I, for example, the sodium and potassium salts, and other like salts well known to the art.
- the preferred acyloxy radicals are those of hydrocarbon carboxylic acids of less than twelve carbon atoms, as exemplified by the lower alkanoic acids, the lower alkenoic acids, the monocyclic aryl carboxylic acids, the monocyclic aryl lower alkanoic acids, the cycloalkane carboxylic acids and the cycloalkene carboxylic acids.
- the preferred alkoxy radicals are those of less than twelve carbon atoms and may be straight or branch chain, and may include such moieties as, methoxy, ethoxy, propoxy, t.-butoxy, pentoxy and the like.
- compositions of this invention are administered to the mammal being treated in a daily amount of from about 25 to about 2.500 milligrams per day.
- the most preferred route of administration of the compositions of this invention is perorally, although other routes of administration may also provide satisfactory results.
- Optimal results may be obtained in the practice of this invention when the compositions of this invention are orally administered to the patient being treated at a daily dosage level of from about 50 to 1500 milligrams, over an extended period sufficient to provide to beneficial results desired.
- the active substances of Formula 1 hereof may be incorporated into 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 administration and preferably oral administration, containing the active substances of Formula I in suflicient 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 are obtained by the use of tablets or capsules containing the active substance in a concentration of from 50 to 500 milligrams each, although other concentrations may also be utilized satisfactorily.
- EXAMPLE 1 Final orally administerable dosage forms incorporating the active substances set forth in Table A below, were prepared and administered on a daily basis to patients in a'hypercholesteremic or hyperlipidemic condition. These compositions were administered to the patients over an extended period of time during which the patients experienced a significant reduction in their cholesterol or lipid levels, without untoward side effects.
- a method for reducing the cholesterol and lipid levels of mammals which comprises:
- R is selected from the group consisting of glycine, taurine, hydroxy, acyloxy and alkoxy; each X is hydrogen; each Y is selected from the group consisting of hydroxy, acyloxy, and alkoxy; when taken together X and Y is oxo wherein each acyloxy radical is from a hydrocarbon carboxylic acid of less than 12 carbon atoms; and the non-toxic, pharmaceutically acceptable salts thereof.
- R is selected from the group consisting of glycine, taurine, hydroxy and acetoxy.
- a pharmaceutical composition useful in the treatment of hypercholesteremia or hyperlipidemia which comprises:
- R, X and Y are as defined in Claim 1; or a non-toxic, pharmaceutically acceptable salt thereof;
- composition suitable for oral administration of the said composition.
- a pharmaceutical composition useful in the treatment of hypercholesteremia or hyperlipidemia which comprises:
- R is selected from the group consisting of glycine, taurine, hydroxy and acyloxy; each X is hydrogen; each Y is selected from the group consisting of hydroxy, acyloxy and alkoxy; X and Y when taken together is 0x0 (0:); wherein each acyloxy radical is from a hydrocarbon carboxylic acid of less than 12 carbon atoms; or the non-toxic, pharmaceutically acceptable salt thereof; and b. a non-toxic, pharmaceutically acceptable carrier, suitable for oral administration of said composition.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1. A METHOD FOR REDUCING THE CHOLESTEROL AND LIPID LEVELS OF MAMMALS WHICH COMPRISES; A. ADMINISTERING TO A MAMMAL IN HYPERCHOLESTEREMIC OR HYPERLIPIDEMIC CONDITION; B. A DAILY DOSAGE OF FROM 25 TO 2500 MG. OF A COMPOUND OF THE FORMULA:
3,7-DI(X),3,7-DI(Y),17-(R-CO-CH2-CH2-CH(-CH3)-)-
ANDROST-11-ENE
WHEREIN R IS SELECTED FROM THE GROUP CONSISTING OF GLYCINE, TAURINE, HYDROXY, ACYLOXY AND ALKOXY; EACH X IS HYDROGEN; EACH Y IS SELECTED FROM THE GROUP CONSISTING OF HYDROXY, ACYLOXY, AND ALKOXY; WHEN TAKEN TOGETHER X AND Y IS OXO (O=); WHEREIN EACH ACYLOXY RADICAL IS FROM A HYDROCARBON CARBOXYLIC ACID OF LESS THAN 12 CARBON ATOMS; AND THE NON-TOXIC, PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF.
3,7-DI(X),3,7-DI(Y),17-(R-CO-CH2-CH2-CH(-CH3)-)-
ANDROST-11-ENE
WHEREIN R IS SELECTED FROM THE GROUP CONSISTING OF GLYCINE, TAURINE, HYDROXY, ACYLOXY AND ALKOXY; EACH X IS HYDROGEN; EACH Y IS SELECTED FROM THE GROUP CONSISTING OF HYDROXY, ACYLOXY, AND ALKOXY; WHEN TAKEN TOGETHER X AND Y IS OXO (O=); WHEREIN EACH ACYLOXY RADICAL IS FROM A HYDROCARBON CARBOXYLIC ACID OF LESS THAN 12 CARBON ATOMS; AND THE NON-TOXIC, PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF.
Description
United States Patent 3,839,565 CHEMICAL PROCESS William H. Saltzman, New Rochelle, N.Y., assignor to Intellectual Property Development Corporation, New Rochelle, N.Y.
No Drawing. Filed Oct. 31, 1972, Ser. No. 302,508 Int. Cl. C07c 169/40 US. Cl. 424-238 12 Claims ABSTRACT OF THE DISCLOSURE A method of reducing the levels of cholesterol and other lipids in mammals, which comprises administering to said mammals an effective amount of a substance having the formula:
wherein R is selected from the group consisting of an amino acid, for example glycine or turine, hydroxy, acyloxy or alkoxy; and each X is hydrogen; and each Y is hydroxy, acyloxy or alkoxy; and when taken together, X and Y is oxo (0:); and the non-toxic, pharmaceutically acceptable salts thereof.
SPECIFICATION l l I I I wherein R is an amino acid, for example,
NHCH CH SO H or NHCH SO H,
hydroxy, acyloxy or alkoxy; each X is hydrogen; Y is hydroxy, acyloxy, or alkoxy; and when taken together, X and Y is 0x0 (0:); and the non-toxic, pharmaceutically acceptable salts thereof. By the practice of this invention, it has been found that it is possible to safely and effectively lower the cholesterol and other lipid levels of the mammals being treated here under. More specifically, it has been found that the administration of effective amounts of the compounds of Formula I above, to mammals in a hyperlipidemic or hypercholesteremic state or condition results in a significant reduction in the cholesterol or lipid levels of the treated mammal. Among those hypercholesteremic and hyperlipidemic states or 3,839,565 Patented Oct. 1, 1974 conditions in which the compositions of this invention have been found to be effective may be included such conditions as hypercholesterolemia, hypertriglyceridemia and cholelithiasis, among others. It has been found that most satisfactory results are obtained when a patient suffering from cholelithiasis, i.e. cholesterol gallstones, is treated with the compositions of this invention. In these cases, it has been discovered that after relatively short periods of treatment with the compositions of this invention, the patients gallstones begin to rapidly dissolve, without the need for surgery.
The preferred compounds of this invention are those of Formula L wherein Y and R are hydroxy, although the other compounds also provide satisfactory results. Among the specific compounds which may be employed in the practice of this invention may be included such compounds as, 3a,7a dihydroxy 5fi-chol-l1-en-24-oic acid, 3a,7a-diacyloxy-5/3-chol-l1-en-24-oic acid, for example, 30:,70: diacetoxy-SB-chol-l1-en-24-oic acid, 3,7-dioxy-5B- chol-11-en-24-oic acid, 3oz acyloxy-7a-hydroxy-5fi-chol- 11-en-24-oic acid, and other like compounds.
The non-toxic, pharmaceutically acceptable salts which may be employed in the practice of this invention include such salts as the alkali metal salts of the compounds of Formula I, for example, the sodium and potassium salts, and other like salts well known to the art.
The preferred acyloxy radicals are those of hydrocarbon carboxylic acids of less than twelve carbon atoms, as exemplified by the lower alkanoic acids, the lower alkenoic acids, the monocyclic aryl carboxylic acids, the monocyclic aryl lower alkanoic acids, the cycloalkane carboxylic acids and the cycloalkene carboxylic acids. The preferred alkoxy radicals are those of less than twelve carbon atoms and may be straight or branch chain, and may include such moieties as, methoxy, ethoxy, propoxy, t.-butoxy, pentoxy and the like.
In the practice of this invention satisfactory results are obtained when the compositions of this invention are administered to the mammal being treated in a daily amount of from about 25 to about 2.500 milligrams per day. The most preferred route of administration of the compositions of this invention is perorally, although other routes of administration may also provide satisfactory results. Optimal results may be obtained in the practice of this invention when the compositions of this invention are orally administered to the patient being treated at a daily dosage level of from about 50 to 1500 milligrams, over an extended period sufficient to provide to beneficial results desired.
To achieve the purposes and objectives of this invention, the active substances of Formula 1 hereof, may be incorporated into such suitable final dosage forms as may be satisfactorily prepared and employed by the worker skilled in the art. Thus, the commonly employed pharmaceutically acceptable dosage forms suitable for administration and preferably oral administration, containing the active substances of Formula I in suflicient 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 are obtained by the use of tablets or capsules containing the active substance in a concentration of from 50 to 500 milligrams each, although other concentrations may also be utilized satisfactorily.
The invention may be further illustrated by the following examples:
EXAMPLE 1 Final orally administerable dosage forms incorporating the active substances set forth in Table A below, were prepared and administered on a daily basis to patients in a'hypercholesteremic or hyperlipidemic condition. These compositions were administered to the patients over an extended period of time during which the patients experienced a significant reduction in their cholesterol or lipid levels, without untoward side effects.
TABLE A Compound: Daily Dosage, Mg. 3a,7u-dihydroxy-5,6-chol-l1-en-24-oic acid 500 3a,7a-dihydroxy-5j8-chol-11-en-24-oic acid 7-50 3a,7a-diaoetoxy-5,8-chol-l1-en-24-oic acid 1000 EXAMPLE 2 Patients suffering from cholelithiasis, i.e. cholesterol gallstones, were treated with the compounds set forth in Table B below, by oral administration thereof over an extended period of time. In each case, the patient being treated experienced a significant reduction in the size of their gallstones.
TABLE B Compound: Daily Dosage, Mg. 3a,7a,dihydroxy-5;8-chol-11-en-24-oic acid 750 The invention may be variously otherwise embodied within the scope of the appended claims.
What is claimed is: 1. A method for reducing the cholesterol and lipid levels of mammals which comprises:
a. Administering to a mammal in hypercholesteremic or hyperlipidemic condition; b. A daily dosage of from 25 to 2500 mg. of a compound of the formula:
wherein R is selected from the group consisting of glycine, taurine, hydroxy, acyloxy and alkoxy; each X is hydrogen; each Y is selected from the group consisting of hydroxy, acyloxy, and alkoxy; when taken together X and Y is oxo wherein each acyloxy radical is from a hydrocarbon carboxylic acid of less than 12 carbon atoms; and the non-toxic, pharmaceutically acceptable salts thereof.
2. The method of Claim 1 wherein each X is hydrogen; and each Y is hydroxy.
3. The method of Claim 1 wherein R is selected from the group consisting of glycine, taurine, hydroxy and acetoxy.
4. The method of Claim 1 wherein R is hydroxy; each X is hydrogen; and each Y is selected from the group consisting of hydroxy, acyloxy and alkoxy, wherein the acyloxy radical is from a hydrocarbon carboxylic acid of less than 12 carbon atoms.
5. The method of Claim 1 wherein the compound is selected from the group consisting of 3a,70c-dihydIOXy- 5fl-cho1-1l-en-24-oic acid; 3a,7a-diacetoxy-5 3-chol-ll-en- 24-oic acid; and 3,7-dioxy-5p-chol-11-en-24-oic acid.
6. The method of Claim 1 wherein the compound is 3a,7a,dihydroxy-5}8-chol-11-en-24-oic acid.
7. A pharmaceutical composition useful in the treatment of hypercholesteremia or hyperlipidemia which comprises:
a. As an active ingredient, a compound of the formula:
wherein R, X and Y are as defined in Claim 1; or a non-toxic, pharmaceutically acceptable salt thereof; and
b. a non-toxic, pharmaceutically acceptable carrier,
suitable for oral administration of the said composition.
8. A pharmaceutical composition useful in the treatment of hypercholesteremia or hyperlipidemia, which comprises:
a. As an active ingredient, a compound of the formula:
wherein R is selected from the group consisting of glycine, taurine, hydroxy and acyloxy; each X is hydrogen; each Y is selected from the group consisting of hydroxy, acyloxy and alkoxy; X and Y when taken together is 0x0 (0:); wherein each acyloxy radical is from a hydrocarbon carboxylic acid of less than 12 carbon atoms; or the non-toxic, pharmaceutically acceptable salt thereof; and b. a non-toxic, pharmaceutically acceptable carrier, suitable for oral administration of said composition. 9. The pharmaceutical composition of Claim 7, wherein R is hydroxy.
10. The pharmaceutical composition of Claim 7, wherein each Y is hydroxy.
11. The pharmaceutical composition of Claim 7, wherein X is hydrogen; R is hydroxy; and each Y is hydroxy.
12. The composition of Claim 7, wherein the compound is selected from the group consisting of 3a,7a-dihydroxy-Sfl-chol-l1-en-24-oic acid; 3a,7u-diacetoxy-5flchodl-11-en-24-oic acid; and 3,7-dioxy-5fl-chol-11-en-24-oic acr References Cited ELBERT L. ROBERTS, Primary Examiner '1 US. Cl. X.R. 260397.l, 397.2
UNITED STATES PATEN OFFICE CERTIFICATE OF CORRECTION Patent No. 5,859 565 I Dated 97A Inventor(s) Wi lliam H. Saltzman It is certified that error appears in the above-identified patent and that said Letters Patent are hereby corrected as shown below:
The, following Claims should be added:
I V v "13. The l, wherein in Step a; the hyperchblester'emicit rel hy b erlipi demie 'cdn diti-on is selected from the grqup consist i r j g'b'f' hy'p erc holest'eriol e'mja, nypertri I glyceridemia arlld ch o lefl-iit h i a si s I I I 14 The pharmaceut ic al eblnposi ti on ef Cleim 7,
he e n the eorhpound its 34 ,7d -dihydrox y-5p -cho1 -1 1 -en -24-0i c acid." I Signed and sealed this 7th day of January-U275.
(SEAL) Attest mccoY M. GIBS ON JR. c. MARSHALL mm:
Attesting Officer Commissioner of Patents USCOMM-DC 60370-P69 FORM PO-1050 (10-69) r u.s, eovie uueuv rnnmns omen; 93 o
Claims (1)
1. A METHOD FOR REDUCING THE CHOLESTEROL AND LIPID LEVELS OF MAMMALS WHICH COMPRISES; A. ADMINISTERING TO A MAMMAL IN HYPERCHOLESTEREMIC OR HYPERLIPIDEMIC CONDITION; B. A DAILY DOSAGE OF FROM 25 TO 2500 MG. OF A COMPOUND OF THE FORMULA:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00302508A US3839565A (en) | 1972-10-31 | 1972-10-31 | Chemical process |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00302508A US3839565A (en) | 1972-10-31 | 1972-10-31 | Chemical process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3839565A true US3839565A (en) | 1974-10-01 |
Family
ID=23168031
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00302508A Expired - Lifetime US3839565A (en) | 1972-10-31 | 1972-10-31 | Chemical process |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3839565A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3931403A (en) * | 1973-05-25 | 1976-01-06 | Intellectual Property Development Corporation | Antimicrobial compositions |
| US4022806A (en) * | 1974-12-23 | 1977-05-10 | The Union International Company Ltd. | Process for preparing chenodeoxycholic acid |
| US4029775A (en) * | 1974-11-14 | 1977-06-14 | Intellectual Property Development Corporation | Antimicrobial compositions |
| US4263272A (en) * | 1978-12-15 | 1981-04-21 | Lehner Ag | Pharmaceutical composition of prolonged action containing bile acids |
| US4939134A (en) * | 1988-09-19 | 1990-07-03 | New York University | 26-aminocholesterol and derivatives and analogs thereof in the regulation of cholesterol accumulation in body tissue |
| US5122520A (en) * | 1988-04-30 | 1992-06-16 | Sandoz Ltd. | Acid addition salts of amidated taurine or glycine, their preparation and use |
| US5274088A (en) * | 1992-07-02 | 1993-12-28 | New York University | Method for the preparation of (25r)-26-aminocholesterol |
-
1972
- 1972-10-31 US US00302508A patent/US3839565A/en not_active Expired - Lifetime
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3931403A (en) * | 1973-05-25 | 1976-01-06 | Intellectual Property Development Corporation | Antimicrobial compositions |
| US4029775A (en) * | 1974-11-14 | 1977-06-14 | Intellectual Property Development Corporation | Antimicrobial compositions |
| US4022806A (en) * | 1974-12-23 | 1977-05-10 | The Union International Company Ltd. | Process for preparing chenodeoxycholic acid |
| US4263272A (en) * | 1978-12-15 | 1981-04-21 | Lehner Ag | Pharmaceutical composition of prolonged action containing bile acids |
| US5122520A (en) * | 1988-04-30 | 1992-06-16 | Sandoz Ltd. | Acid addition salts of amidated taurine or glycine, their preparation and use |
| US4939134A (en) * | 1988-09-19 | 1990-07-03 | New York University | 26-aminocholesterol and derivatives and analogs thereof in the regulation of cholesterol accumulation in body tissue |
| US5274088A (en) * | 1992-07-02 | 1993-12-28 | New York University | Method for the preparation of (25r)-26-aminocholesterol |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
Owner name: CHOLEX LABORATORIES, INC.; A CORP OF NY. Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:INTELLECTUAL PROPERTY DEVELOPMENT CORPORATION;REEL/FRAME:004113/0452 Effective date: 19821220 |