US3600495A - Medicament preparation and process for the manufacture thereof - Google Patents
Medicament preparation and process for the manufacture thereof Download PDFInfo
- Publication number
- US3600495A US3600495A US744675A US3600495DA US3600495A US 3600495 A US3600495 A US 3600495A US 744675 A US744675 A US 744675A US 3600495D A US3600495D A US 3600495DA US 3600495 A US3600495 A US 3600495A
- Authority
- US
- United States
- Prior art keywords
- gastric
- manufacture
- androsterone
- dehydro
- epi
- 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
- 238000000034 method Methods 0.000 title description 5
- 238000004519 manufacturing process Methods 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 3
- 239000003814 drug Substances 0.000 title description 2
- 230000003054 hormonal effect Effects 0.000 abstract description 10
- 230000007935 neutral effect Effects 0.000 abstract description 9
- -1 sulpho Chemical class 0.000 description 17
- 210000004051 gastric juice Anatomy 0.000 description 11
- 239000011248 coating agent Substances 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- 150000003431 steroids Chemical class 0.000 description 9
- FMGSKLZLMKYGDP-UHFFFAOYSA-N Dehydroepiandrosterone Natural products C1C(O)CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CC=C21 FMGSKLZLMKYGDP-UHFFFAOYSA-N 0.000 description 7
- ORNBQBCIOKFOEO-YQUGOWONSA-N Pregnenolone Natural products O=C(C)[C@@H]1[C@@]2(C)[C@H]([C@H]3[C@@H]([C@]4(C)C(=CC3)C[C@@H](O)CC4)CC2)CC1 ORNBQBCIOKFOEO-YQUGOWONSA-N 0.000 description 7
- FMGSKLZLMKYGDP-USOAJAOKSA-N dehydroepiandrosterone Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 FMGSKLZLMKYGDP-USOAJAOKSA-N 0.000 description 7
- 229960002847 prasterone Drugs 0.000 description 7
- 229960000249 pregnenolone Drugs 0.000 description 7
- ORNBQBCIOKFOEO-QGVNFLHTSA-N pregnenolone Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 ORNBQBCIOKFOEO-QGVNFLHTSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 6
- 239000002552 dosage form Substances 0.000 description 5
- 229940088597 hormone Drugs 0.000 description 5
- 239000005556 hormone Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229910021653 sulphate ion Inorganic materials 0.000 description 5
- 208000024891 symptom Diseases 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- CZWCKYRVOZZJNM-USOAJAOKSA-N dehydroepiandrosterone sulfate Chemical compound C1[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 CZWCKYRVOZZJNM-USOAJAOKSA-N 0.000 description 3
- 229920000867 polyelectrolyte Polymers 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 229920000623 Cellulose acetate phthalate Polymers 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 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 2
- 241000124008 Mammalia Species 0.000 description 2
- 206010027304 Menopausal symptoms Diseases 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- CZWCKYRVOZZJNM-UHFFFAOYSA-N Prasterone sodium sulfate Natural products C1C(OS(O)(=O)=O)CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CC=C21 CZWCKYRVOZZJNM-UHFFFAOYSA-N 0.000 description 2
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229940081734 cellulose acetate phthalate Drugs 0.000 description 2
- 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 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
- ZESRJSPZRDMNHY-YFWFAHHUSA-N 11-deoxycorticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 ZESRJSPZRDMNHY-YFWFAHHUSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- 206010020112 Hirsutism Diseases 0.000 description 1
- 102000011782 Keratins Human genes 0.000 description 1
- 108010076876 Keratins Proteins 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229920001800 Shellac Polymers 0.000 description 1
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- ZESRJSPZRDMNHY-UHFFFAOYSA-N de-oxy corticosterone Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 ZESRJSPZRDMNHY-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 229960003654 desoxycortone Drugs 0.000 description 1
- 208000002173 dizziness Diseases 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002085 enols Chemical group 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000001087 glyceryl triacetate Substances 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 206010022437 insomnia Diseases 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N n-hexadecyl alcohol Natural products CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- 229960004719 nandrolone Drugs 0.000 description 1
- NPAGDVCDWIYMMC-IZPLOLCNSA-N nandrolone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 NPAGDVCDWIYMMC-IZPLOLCNSA-N 0.000 description 1
- 239000002929 natural lacquer Substances 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229950009829 prasterone sulfate Drugs 0.000 description 1
- 239000000186 progesterone Substances 0.000 description 1
- 229960003387 progesterone Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229960003604 testosterone Drugs 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000005068 transpiration Effects 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
- A61K9/2806—Coating materials
- A61K9/2833—Organic macromolecular compounds
- A61K9/286—Polysaccharides, e.g. gums; Cyclodextrin
- A61K9/2866—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
Definitions
- BACKGROUND OF THE INVENTION Disturbances of the normal hormonal equilibrium in warm-blooded mammals is manifested by various diseases and disturbances of varying degrees of severity. For example, in the climacteric, including the preand postclimacteric periods, the symptoms and/ or the corresponding pathological deficiencies Which occur are attributable to a disturbance of the hormonal equilibrium. Decreasing vitality With increasing age is likewise attributable to a disturbance in the normal hormonal equilibrium. Some dematological manifestations are also hormone-dependent, for example, hirsutism seems to be caused by a hormonal imbalance.
- sulphoconjugated neutral steroids mean non-phenolic steroids Which are esterified with sulphuric acid or with sulphuric acid derivatives, i.e., the sulphates or sulphatides of the steroids.
- non-phenolic steroids are, for example, cholesterol, C -steroids such as pregnenolone, desoxycorticosterone, progesterone (in enol form), C -steroids such as dehydro-epi-androsterone, testosterone, C -steroids such as 19-nortestosterone.
- Particularly preferred compounds useful in the practice of this invention are pregnenolone and dehydro-epi-androsterone in the form of the sulphate or sulphatide.
- Sulphates as used herein include both the acidic sulphates and the mixed salts of sulphuric acid with a nontoxic pharmaceutically acceptable cation such as, for example, ammonium, sodium, potassium and calcium.
- a nontoxic pharmaceutically acceptable cation such as, for example, ammonium, sodium, potassium and calcium.
- the alcoholic part of the ester must be derived from a non-toxic pharmaceutically acceptable monovalent or polyvalent alcohol, e.g., from glycerine or higher fatty alcohols such as palmityl or stearyl alcohol.
- composition of this invention in unit dosage form is controlled by the particular needs of the patients and by the symptoms and disease being treated as Well as by the specific active substance being used.
- a dosage of between about mg. and about 30 mg. of dehydro-epi-androsterone 3- sulphate per day has proven efficacious for influencing menopausal symptoms as it is evident from Table I and II:
- gastric-juice-resistant composition is conventional.
- polyelectrolytes containing carboxyl groups are used.
- natural lacquers such as keratin, shellac, collophony
- cellulose esters containing carboxyl groups such as acetyl-phthalyl-cellulose, acetyl-succinyl-cellulose
- copolymers containing carboxyl groups which contain maleic acid as the acid component such as copolymers of styrene and maleic acid anhydride, copolymers of butyl partial ester of maleic acid with styrene and small amounts of acrylic acid, copolymers of maleic acid anhydride and vinyl methyl ether
- copolymers containing carboxyl groups which contain acrylic acid or methacrylic acid as the acid component such as copolymers of styrene and methacrylic acid.
- the manufacture of the unit dosage form used in this invention is achieved by conventional methods using conventional equipment.
- the film-forming material which is resistant to gastric juice is brought into solution by means of a solvent.
- Any medicinally acceptable solvent in which the film-forming material is soluble can be used for the manufacture of the solution.
- cellulose acetate phthalate is used as the gastricjuice-resistant coating material
- methylene chloride usually mixed with a small amount of a lower alkanol, is advantageously used as the solvent.
- the concentration of the solution used can vary within wide limits. However, it is convenient that the solution contain about 7 to 12 parts by weight of solvent per part by weight of coating material.
- the coating procedure is conventional.
- the nucleus, in tablet form, containing the sulpho-conjugated neutral steroid is treated with the solution containing the coating material in a coating drum. By rotation of the coating drum, a thin uniform coating is produced on the tablets.
- the coated tablets are subsequently dried and this coating-drying process repeated several times until a sufiicient layer of the gastric-juice-resistant coating is present on the tablets to ensure that the tablets will be unaffected by gastric-sjuice.
- the invention is illustrated by the following example.
- Dragee nuclei of 75 mg. weight and a diameter of 6 mm. containing 10.0 mg. of sodium dehydro-epi-androsterone sulphate, 50.00 mg. of lactose, 13.50 mg. of corn starch, 1.35 mg. of talc and 0.15 mg. of magnesium stearate per nucleus are formed and coated with a gastricjuice-resistant lacquer layer by using a lacquer solution consisting of parts by weight of cellulose acetate phthalate, 3 parts by weight of triacetin, 10 parts by weight of ethanol and 77 parts by weight of methylene chloride. A suflic'ient resistance to gastric juices is ensured by application of about 25 layers.
- the coating amounts to about 10 mg. per nucleus.
- the lacquered nuclei obtained are dried at about 37 C. for 24-36 hours and then dredged until they have an end weight of about mg.
- composition according to claim 1 wherein said steroid compound is dehydro-epi-androsterone in the form of sulphate.
- composition according to claim 1 wherein said steroid compound is pregnenolone in the form of a sulphate.
- composition according to claim 1 wherein said steroid compound is pregnenolone in the form of a sulphatide.
- a sulpho-conjugated neutral steroid compound selected from the group consisting of the sulphates and sulphatides of dehydro-epi-androsterone and pregnenolone, the improvement which comprises administering said steroid in the form of a tablet nucleus which is coated with a gastric-juice-resistant layer of polyelectrolytes containing carboxyl groups.
- said steroid compound is selected from the group consisting of dehydro-epi-androsterone, the sulphate thereof and the sulphatide thereof.
- said steroid compound is selected from the group consisting of pregnenolone, the sulphate thereof and the sulphatide thereof.
Landscapes
- Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1075567 | 1967-07-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3600495A true US3600495A (en) | 1971-08-17 |
Family
ID=4366476
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US744675A Expired - Lifetime US3600495A (en) | 1967-07-28 | 1968-07-15 | Medicament preparation and process for the manufacture thereof |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3600495A (OSRAM) |
| BE (1) | BE718543A (OSRAM) |
| DE (1) | DE1767898A1 (OSRAM) |
| FR (1) | FR8158M (OSRAM) |
| GB (1) | GB1188629A (OSRAM) |
| NL (1) | NL6809629A (OSRAM) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6024982A (en) * | 1993-11-23 | 2000-02-15 | Euro-Celtique, S.A. | Immediate release tablet cores of insoluble drugs having sustained-release coating |
| US6387404B2 (en) | 1993-11-23 | 2002-05-14 | Euro-Celtique S.A. | Immediate release tablet cores of insoluble drugs having sustained-release coating |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE439586B (sv) * | 1975-09-05 | 1985-06-24 | Kanebo Ltd | Sett att framstella ett stabilt farmaceutiskt torrpreparat av ett alkalimetallsalt av dehydroepiandrosteronsulfat |
-
1968
- 1968-06-28 DE DE19681767898 patent/DE1767898A1/de active Pending
- 1968-07-08 NL NL6809629A patent/NL6809629A/xx unknown
- 1968-07-15 US US744675A patent/US3600495A/en not_active Expired - Lifetime
- 1968-07-18 GB GB34358/68A patent/GB1188629A/en not_active Expired
- 1968-07-25 BE BE718543D patent/BE718543A/xx unknown
- 1968-07-29 FR FR160942A patent/FR8158M/fr not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6024982A (en) * | 1993-11-23 | 2000-02-15 | Euro-Celtique, S.A. | Immediate release tablet cores of insoluble drugs having sustained-release coating |
| US6387404B2 (en) | 1993-11-23 | 2002-05-14 | Euro-Celtique S.A. | Immediate release tablet cores of insoluble drugs having sustained-release coating |
Also Published As
| Publication number | Publication date |
|---|---|
| FR8158M (OSRAM) | 1970-08-24 |
| DE1767898A1 (de) | 1971-09-30 |
| BE718543A (OSRAM) | 1969-01-27 |
| NL6809629A (OSRAM) | 1969-01-30 |
| GB1188629A (en) | 1970-04-22 |
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