GB916778A - Oral compositions containing 3-substituted 17-ª--methyl testosterones - Google Patents
Oral compositions containing 3-substituted 17-ª--methyl testosteronesInfo
- Publication number
- GB916778A GB916778A GB34990/59A GB3499059A GB916778A GB 916778 A GB916778 A GB 916778A GB 34990/59 A GB34990/59 A GB 34990/59A GB 3499059 A GB3499059 A GB 3499059A GB 916778 A GB916778 A GB 916778A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- tertosterone
- enol
- ethyl
- alkyl
- 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
Links
- 239000000203 mixture Substances 0.000 title abstract 5
- -1 cycloalkyl ethers Chemical class 0.000 abstract 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 5
- 125000004432 carbon atom Chemical group C* 0.000 abstract 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 5
- 239000003925 fat Substances 0.000 abstract 4
- 235000019197 fats Nutrition 0.000 abstract 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 3
- GCKMFJBGXUYNAG-HLXURNFRSA-N Methyltestosterone Chemical class C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@](C)(O)[C@@]1(C)CC2 GCKMFJBGXUYNAG-HLXURNFRSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 3
- 239000003921 oil Substances 0.000 abstract 3
- 235000019198 oils Nutrition 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 abstract 2
- 239000004480 active ingredient Substances 0.000 abstract 2
- 230000001548 androgenic effect Effects 0.000 abstract 2
- AEMFNILZOJDQLW-QAGGRKNESA-N androst-4-ene-3,17-dione Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 AEMFNILZOJDQLW-QAGGRKNESA-N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 150000002632 lipids Chemical group 0.000 abstract 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 abstract 2
- 239000001195 (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid Substances 0.000 abstract 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- 241001133760 Acoelorraphe Species 0.000 abstract 1
- 235000017060 Arachis glabrata Nutrition 0.000 abstract 1
- 244000105624 Arachis hypogaea Species 0.000 abstract 1
- 235000010777 Arachis hypogaea Nutrition 0.000 abstract 1
- 235000018262 Arachis monticola Nutrition 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 1
- 244000060011 Cocos nucifera Species 0.000 abstract 1
- 235000013162 Cocos nucifera Nutrition 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- 102000002322 Egg Proteins Human genes 0.000 abstract 1
- 108010000912 Egg Proteins Proteins 0.000 abstract 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- 241000173371 Garcinia indica Species 0.000 abstract 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 abstract 1
- 244000068988 Glycine max Species 0.000 abstract 1
- 235000010469 Glycine max Nutrition 0.000 abstract 1
- 108010076876 Keratins Proteins 0.000 abstract 1
- 102000011782 Keratins Human genes 0.000 abstract 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 abstract 1
- 240000006240 Linum usitatissimum Species 0.000 abstract 1
- 235000004431 Linum usitatissimum Nutrition 0.000 abstract 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 abstract 1
- 240000007817 Olea europaea Species 0.000 abstract 1
- 235000003434 Sesamum indicum Nutrition 0.000 abstract 1
- 244000000231 Sesamum indicum Species 0.000 abstract 1
- 235000021307 Triticum Nutrition 0.000 abstract 1
- 244000098338 Triticum aestivum Species 0.000 abstract 1
- 240000008042 Zea mays Species 0.000 abstract 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 abstract 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 abstract 1
- 239000003377 acid catalyst Substances 0.000 abstract 1
- 239000002671 adjuvant Substances 0.000 abstract 1
- 125000002723 alicyclic group Chemical group 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 abstract 1
- 239000003263 anabolic agent Substances 0.000 abstract 1
- 239000003098 androgen Substances 0.000 abstract 1
- 230000002421 anti-septic effect Effects 0.000 abstract 1
- 239000003963 antioxidant agent Substances 0.000 abstract 1
- 229940064004 antiseptic throat preparations Drugs 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 abstract 1
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 235000019868 cocoa butter Nutrition 0.000 abstract 1
- 229940110456 cocoa butter Drugs 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 235000005822 corn Nutrition 0.000 abstract 1
- 235000012343 cottonseed oil Nutrition 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical class C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 235000013345 egg yolk Nutrition 0.000 abstract 1
- 210000002969 egg yolk Anatomy 0.000 abstract 1
- 150000002084 enol ethers Chemical class 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 235000004426 flaxseed Nutrition 0.000 abstract 1
- 235000021588 free fatty acids Nutrition 0.000 abstract 1
- 229930182830 galactose Natural products 0.000 abstract 1
- 239000007903 gelatin capsule Substances 0.000 abstract 1
- 239000008103 glucose Substances 0.000 abstract 1
- 125000003827 glycol group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229940088597 hormone Drugs 0.000 abstract 1
- 239000005556 hormone Substances 0.000 abstract 1
- 239000008101 lactose Substances 0.000 abstract 1
- 150000004668 long chain fatty acids Chemical class 0.000 abstract 1
- 235000019359 magnesium stearate Nutrition 0.000 abstract 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 abstract 1
- 235000013310 margarine Nutrition 0.000 abstract 1
- 239000003264 margarine Substances 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 235000021313 oleic acid Nutrition 0.000 abstract 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 abstract 1
- OEOFQABUOAWYMP-UHFFFAOYSA-N oxiren-2-ol Chemical compound OC1=CO1 OEOFQABUOAWYMP-UHFFFAOYSA-N 0.000 abstract 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 abstract 1
- 235000020232 peanut Nutrition 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 239000003755 preservative agent Substances 0.000 abstract 1
- 239000000473 propyl gallate Substances 0.000 abstract 1
- 229940075579 propyl gallate Drugs 0.000 abstract 1
- 235000010388 propyl gallate Nutrition 0.000 abstract 1
- 229940100486 rice starch Drugs 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 235000020238 sunflower seed Nutrition 0.000 abstract 1
- 239000006188 syrup Substances 0.000 abstract 1
- 235000020357 syrup Nutrition 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
- 239000000454 talc Substances 0.000 abstract 1
- 229910052623 talc Inorganic materials 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
- 235000013311 vegetables Nutrition 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Preparation (AREA)
Abstract
The invention comprises inter alia the 3-enol alkyl or cycloalkyl ethers of free or acylated 17a -methyl testosterone having from 4-8 carbon atoms in the alkyl or cycloalkyl group. The compounds are prepared by (a) reacting methyl magnesium bromide with the corresponding enol ether of androstene-3,17-dione or (b) reacting the appropriate alcohol with the 3-enol ethyl ether of 17a -methyl testerone free or acylated in the presence of an acid catalyst, e.g. p-toluene sulphonic acid. The above process (b) may be used to prepare other 3-enol alkyl and benzyl ethers of 17a -methyltestosterone especially those substituted with functional substituents such as nitro and halo substituents. 3-Alkylene ketals of 17a -methyltestosterone are prepared by reacting 3-alkylene ketals of D 4-androstene-3,17-dione with methyl magnesium halide.ALSO:An oral composition having a high androgenic and anobolic activity comprises a 3-enol ether or a 3-glycol ketal of 17a methyl tertosterone or a 17b ester thereof, mixed with an orally ingestible pharmaceutical carrier. The 3-enol ether of tertosterone has at the 3 position a residue of an aliphatic, alicyclic arylaliphatic, aromatic or heterocyclic alcohol. The residue may contain a straight or branch chain alkyl group, which may be substituted e.g. by halogen; an alkylene group e.g. ethylene, a tetrahydropyraryl group or maybe a sugar residue such as that of glucose, galactose or maltose. Preferred ethers have a straight alkyl chain of 4 to 8 carbon atoms with or without methyl or ethyl substituents, at the 3 position. Preferred glycol ketals are alkylene glycol ketals having 2 to 4 carbon atoms in the glycol group. The compositions may be in the form of coated or uncoated tablets, powders, syrups and capsules e.g. keratin or gelatin capsules and are stabilised by adding an alkaline oxide e.g. MgO or an alkaline carbonate. The preferred carrier is a lipid from animal or vegetable sources, specified lipid carriers are (a) oils e.g. coconut, corn, cottonseed, lard, linseed, olive, sunflower seed, palm, peanut, sesame, soya bean, wheat germ and egg yolk oil. (b) Fats e.g. butter fat, lard, cocoa butter or margarine fat; (c) esters of glycerol with high molecular weight long chain fatty acids of 10-22 C atoms; (d) the free fatty acids contained in fats or oils having 10 to 22 carbon atoms e.g. decenoic, decosanoic lauric, palmitic, stearic, archidic, oleic, linoleic and linolenic acids. Other adjuvants specified are magnesium stearate, talc, lactose, rice starch. The compositions may also contain androgenic and/or anabolic steroid hormones, antiseptics, antioxidants e.g. propyl gallate and/or preservatives. The active ingredient is present in an amount ranging from 0.1 to 7% by weight of the final composition. Specified active ingredients are the 3-sec.-butyl, 3-n-amyl -, 3 isoamyl -, 3 hexyl -, 3 - (2 - methyl) pentyl -, 3 - n - heptyl -, 3 cyclohexyl -, 3 benzyl -, 3 - isobutyl -, 3 - sec - (3,3 - dimethyl)-butyl -, 3 - (2 - ethyl) - butyl, 3 - octyl, 3-chloroethyl, 3 - n - butyl and 3 ethyl enol ether of 17a methyl tertosterone, the 3-ethyl-enol ether of 17a methyl tertosterone acetate and the 3 glycol ketal of 17a methyl tertosterone.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB34990/59A GB916778A (en) | 1959-10-15 | 1959-10-15 | Oral compositions containing 3-substituted 17-ª--methyl testosterones |
| BE590424A BE590424A (en) | 1959-05-04 | 1960-05-03 | Hormonal compositions. |
| CH504460A CH389595A (en) | 1959-05-04 | 1960-05-03 | Process for the preparation of enol ethers of 4-3-keto steroids |
| AT334760A AT243446B (en) | 1959-05-04 | 1960-05-03 | Process for the preparation of enol ethers of Δ <4> -3-keto steroids |
| FR837301A FR568M (en) | 1959-05-04 | 1960-08-31 | |
| OA51016A OA00921A (en) | 1959-10-15 | 1964-12-24 | A process for the preparation of 2-enole ethers of 17α-methyl testosterone. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB34990/59A GB916778A (en) | 1959-10-15 | 1959-10-15 | Oral compositions containing 3-substituted 17-ª--methyl testosterones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB916778A true GB916778A (en) | 1963-01-30 |
Family
ID=10372503
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB34990/59A Expired GB916778A (en) | 1959-05-04 | 1959-10-15 | Oral compositions containing 3-substituted 17-ª--methyl testosterones |
Country Status (2)
| Country | Link |
|---|---|
| GB (1) | GB916778A (en) |
| OA (1) | OA00921A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996037201A3 (en) * | 1995-05-16 | 1997-01-03 | Arch Dev Corp | METHODS AND COMPOSITIONS FOR INHIBITING 5α-REDUCTASE ACTIVITY |
| WO2000066612A1 (en) * | 1999-05-04 | 2000-11-09 | Strakan Limited | Androgen glycosides and androgenic activity thereof |
| US8466138B2 (en) | 2005-10-12 | 2013-06-18 | Unimed Pharmaceuticals, Llc | Testosterone gel and method of use |
| US9125816B2 (en) | 2000-08-30 | 2015-09-08 | Besins Healthcare Inc. | Pharmaceutical composition and method for treating hypogonadism |
-
1959
- 1959-10-15 GB GB34990/59A patent/GB916778A/en not_active Expired
-
1964
- 1964-12-24 OA OA51016A patent/OA00921A/en unknown
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996037201A3 (en) * | 1995-05-16 | 1997-01-03 | Arch Dev Corp | METHODS AND COMPOSITIONS FOR INHIBITING 5α-REDUCTASE ACTIVITY |
| WO2000066612A1 (en) * | 1999-05-04 | 2000-11-09 | Strakan Limited | Androgen glycosides and androgenic activity thereof |
| US6630453B1 (en) | 1999-05-04 | 2003-10-07 | Strakan Limited | Androgen derivatives and uses thereof |
| US6916791B2 (en) | 1999-05-04 | 2005-07-12 | Strakan Limited | Androgen derivatives and uses thereof |
| US9132089B2 (en) | 2000-08-30 | 2015-09-15 | Besins Healthcare Inc. | Pharmaceutical composition and method for treating hypogonadism |
| US9125816B2 (en) | 2000-08-30 | 2015-09-08 | Besins Healthcare Inc. | Pharmaceutical composition and method for treating hypogonadism |
| US8466137B2 (en) | 2005-10-12 | 2013-06-18 | Unimed Pharmaceuticals, Llc | Testosterone gel and method of use |
| US8486925B2 (en) | 2005-10-12 | 2013-07-16 | Unimed Pharmaceuticals, Llc | Testosterone gel and method of use |
| US8729057B2 (en) | 2005-10-12 | 2014-05-20 | Unimed Pharmaeuticals, LLC | Testosterone gel and method of use |
| US8741881B2 (en) | 2005-10-12 | 2014-06-03 | Unimed Pharmaceuticals, Llc | Testosterone gel and method of use |
| US8754070B2 (en) | 2005-10-12 | 2014-06-17 | Unimed Pharmaceuticals, Llc | Testosterone gel and method of use |
| US8759329B2 (en) | 2005-10-12 | 2014-06-24 | Unimed Pharmaceuticals, Llc | Testosterone gel and method of use |
| US8466136B2 (en) | 2005-10-12 | 2013-06-18 | Unimed Pharmaceuticals, Llc | Testosterone gel and method of use |
| US8466138B2 (en) | 2005-10-12 | 2013-06-18 | Unimed Pharmaceuticals, Llc | Testosterone gel and method of use |
Also Published As
| Publication number | Publication date |
|---|---|
| OA00921A (en) | 1968-03-22 |
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