US2173337A - Preparation having enhanced sexual hormone action and process of making same - Google Patents
Preparation having enhanced sexual hormone action and process of making same Download PDFInfo
- Publication number
- US2173337A US2173337A US125122A US12512237A US2173337A US 2173337 A US2173337 A US 2173337A US 125122 A US125122 A US 125122A US 12512237 A US12512237 A US 12512237A US 2173337 A US2173337 A US 2173337A
- Authority
- US
- United States
- Prior art keywords
- acid
- preparation
- hormone action
- sexual hormone
- making same
- 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
- 239000003163 gonadal steroid hormone Substances 0.000 title description 8
- 238000002360 preparation method Methods 0.000 title description 8
- 238000000034 method Methods 0.000 title 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 14
- 150000001875 compounds Chemical class 0.000 description 10
- 229960003604 testosterone Drugs 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 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 description 3
- 229960005471 androstenedione Drugs 0.000 description 3
- AEMFNILZOJDQLW-UHFFFAOYSA-N androstenedione Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 AEMFNILZOJDQLW-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229940088597 hormone Drugs 0.000 description 3
- 239000005556 hormone Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- -1 propane diol mono-palmitic acid ester Chemical class 0.000 description 3
- 239000008159 sesame oil Substances 0.000 description 3
- 235000011803 sesame oil Nutrition 0.000 description 3
- DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 description 2
- GCKMFJBGXUYNAG-UHFFFAOYSA-N 17alpha-methyltestosterone Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(C)(O)C1(C)CC2 GCKMFJBGXUYNAG-UHFFFAOYSA-N 0.000 description 2
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 2
- CBMYJHIOYJEBSB-YSZCXEEOSA-N 5alpha-androstane-3beta,17beta-diol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@H]21 CBMYJHIOYJEBSB-YSZCXEEOSA-N 0.000 description 2
- QADHLRWLCPCEKT-UHFFFAOYSA-N Androstenediol Natural products C1C(O)CCC2(C)C3CCC(C)(C(CC4)O)C4C3CC=C21 QADHLRWLCPCEKT-UHFFFAOYSA-N 0.000 description 2
- GCKMFJBGXUYNAG-HLXURNFRSA-N Methyltestosterone Chemical compound 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 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 235000021314 Palmitic acid Nutrition 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
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- QADHLRWLCPCEKT-LOVVWNRFSA-N androst-5-ene-3beta,17beta-diol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC=C21 QADHLRWLCPCEKT-LOVVWNRFSA-N 0.000 description 2
- 229950009148 androstenediol Drugs 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 2
- 229930182833 estradiol Natural products 0.000 description 2
- 229960003399 estrone Drugs 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229960001566 methyltestosterone Drugs 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- 230000001568 sexual effect Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- DPUOLQHDNGRHBS-MDZDMXLPSA-N trans-Brassidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-MDZDMXLPSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QZLYKIGBANMMBK-UGCZWRCOSA-N 5α-Androstane Chemical compound C([C@@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CCC[C@@]2(C)CC1 QZLYKIGBANMMBK-UGCZWRCOSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- VUXNZDYAHSFXBM-UHFFFAOYSA-N docos-13-ynoic acid Chemical compound CCCCCCCCC#CCCCCCCCCCCCC(O)=O VUXNZDYAHSFXBM-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000002515 guano Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 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
- 239000000186 progesterone Substances 0.000 description 1
- 229960003387 progesterone Drugs 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
Classifications
-
- 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
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
Definitions
- This invention relates to the manufacture of preparations for parenteral use having enhanced sexual hormone action by combining sexual hormones or their derivatives with a compound containing a carboxylic hydroxyl, an alcoholic hydroxyl or a carbonyl group, such as carboxylic acids, monoor dihydric alcohols, ketones or aldehydes. Both saturated compounds and compounds containing double or treble lin'kings have proved efiective.
- the following table shows the effect of such activators on, for example, the action of the testosterone on young castrated rats (the weight of a rat at the time of castration was to grams; the experiment began 30 days after the castration).
- the animals received during 10 days daily each a subcutaneous injection of 50 'y of testosterone and the stated quantity of the compound named dissolved in 0.5 cc. of sesame oil. On the 11th day they were examined.
- oils or other solvents suitable for the parenteral introduction of medicaments or mixtures of such solvents may be used.
- substituted or unsubstituted carboxylic acids monoor divalent alcohols, ethers, ketones or aldehydes, particularly those of the aliphatic series but also those of .a fatty aromatic nature, may be used alone or in combination with each other.
- free acids their salts or esters with poly-alcohols or poly-oxy-ketones, these esters containing at least one free hydroxyl group, may be used, for instance the propane diol mono-palmitic acid ester, the glycerol monoor di-palmitic acid ester or the like.
- the substituted compounds may contain one or more subtives, for example oestrone, oestradiol and their esters as well as with progesterone.
- the new preparations are useful in therapeutics as sexual hormone preparations.
- Preparations for parenteral use having enhanced sexual hormone action obtained by combining a sexual hormone selected from the group consisting of testosterone, androstane-diol, androstene-diol, l7-methyl-testosterone, oestrone, oestradiol and androstene-dione with a compound selected from the group consisting of aliphatic carboxylic acids, aliphatic hydroxy-carboxylic acids and aliphatic alcohols.
- Preparations for parenteral use having enhanced male sexual hormone action obtained by combining testosterone with higher aliphatic
- Preparations for parenteral use having encarboxylic acids. hanced male sexual hormone action obtained 3.
- Preparations for parenteral use having enby combining testosterone with higher aliphatic hanced male sexual hormone action obtained alcohols.
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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)
- Medicinal Preparation (AREA)
- Steroid Compounds (AREA)
Description
Patented Sept. 19, 1939 UNITED STATES PATENT OFFICE HORMONE MAKING SAME Karl Miescher, Riehen,
Basel, Switzerland,
Switzerland No Drawing.
ACTION AND PROCESS OF and Albert Wettstein,
assignors to the firm of S0- ciety of Chemical Industry in Basle, Basel,
Application February 10, 1937, Se-
rial No. 125,122. In Switzerland February 25,
1936 4 Claims.
This invention relates to the manufacture of preparations for parenteral use having enhanced sexual hormone action by combining sexual hormones or their derivatives with a compound containing a carboxylic hydroxyl, an alcoholic hydroxyl or a carbonyl group, such as carboxylic acids, monoor dihydric alcohols, ketones or aldehydes. Both saturated compounds and compounds containing double or treble lin'kings have proved efiective.
The following table shows the effect of such activators on, for example, the action of the testosterone on young castrated rats (the weight of a rat at the time of castration was to grams; the experiment began 30 days after the castration). The animals received during 10 days daily each a subcutaneous injection of 50 'y of testosterone and the stated quantity of the compound named dissolved in 0.5 cc. of sesame oil. On the 11th day they were examined.
Weight in mg. Daily Compounds Formula dose in mg Seminal Prosvesicles tates w-hydroxy-tridecanoic acid. C1:H:t0a 10 132 124 whydror- -margaric acid-.. CHEMOL. 20 184 194 whydroxy-palmitic apid. Guano," 25 150 158 Pyruvic acid (3311403... 10 Q0 Pahnitic acid 0111111103.. 50 260 209 l2-hydroxy-steeric acid. ,CiaHuOaU Ricino'elnidic acid CnHi4O:.. 50 195 207 Stearic acid... CnHaaCa. 50 175 182 Behenolic acid C1zH|aO: 50 160 180 Camphor-Zi-carboxylic acid. CuHmOa-. 25 106 124 l2-ketostearic acid CnHnOz.. 25 125 50 160 186 Elaidic acid 013K140. 10 34 58 5 30 57 50 150 160 25 80 Brassidic acid. CnH4302-- 10 73 93 5 45 66 1 43 53 Bressidic acid without 50 14 38 CaHaOa- 1O 60 8O CnHx:O: 50 12B 178 CaHoOs--. 50 117 158 CiaHMOL- 50 111 129 u-crotonic acid 04111301. 50 90 124 50 85 109 Erucic acid CnHlaOL. 10 47 71 5 44 61 Oleic acid CnHu0a.. 50 60 73 Linoleic acld CuHu0: 50 53 B5 Ethyl alcohol-" C:HuO 50 82 98 Prcpyl alcohol'. 031130-..- 50 117 156 lsopropyl alcohol. CsHsO 50 120 150 Butyl alcohol. C4Hm 50 72 Hexyl alcohol, CoHu0 50 95 125 Octyl alcohol. CBHuO 50 77 Dodecyl alcohol. CnHa 50 95 98 Cetyl aloohol CisHn 50 165 Stearic slcohoL. nHnO... 50 200 220 Olelc alcohol CnHu 50 87 111 Cinnaniic alcohoL. CIHIO 50 80 81 Testosterone alone- 42 66 Sesame oil 14 41 Similar values were attained in combination with androstane diol, androstene-diol, andro stene-dione, methyl-testosterone or the like, as follows for example from the following table:
' With 50 mg. figgg gfi palmitic acid Daily weight in mg. g 'g Compounds dose Seminal Pros- Seminal Prosv tates v tates 17-methylt estosterone 50 58 88 160 210 l7-ethyld1hydrotestos- 500 49 108 70 148 terone 200 19 55 40 60 Androstane 3 cis 17 trans-dial. '200 74 239 308 Androstene-3-trans-l7- 1000 48 71 114 136 trans-diol. 500 30 50 99 120 Androstenedione 500 126 166 208 251 Values obtained with brassidic acid instead of palmitic acid.
Instead of sesame oil other oils or other solvents suitable for the parenteral introduction of medicaments or mixtures of such solvents may be used. Instead of the compounds listed above other substituted or unsubstituted carboxylic acids, monoor divalent alcohols, ethers, ketones or aldehydes, particularly those of the aliphatic series but also those of .a fatty aromatic nature, may be used alone or in combination with each other. Instead of the free acids their salts or esters with poly-alcohols or poly-oxy-ketones, these esters containing at least one free hydroxyl group, may be used, for instance the propane diol mono-palmitic acid ester, the glycerol monoor di-palmitic acid ester or the like. The substituted compounds may contain one or more subtives, for example oestrone, oestradiol and their esters as well as with progesterone.
Instead of the natural sexual hormones artificially made compounds of analogous'action may be similarly used. 1
The new preparations are useful in therapeutics as sexual hormone preparations.
What we claim is:
1. Preparations for parenteral use having enhanced sexual hormone action, obtained by combining a sexual hormone selected from the group consisting of testosterone, androstane-diol, androstene-diol, l7-methyl-testosterone, oestrone, oestradiol and androstene-dione with a compound selected from the group consisting of aliphatic carboxylic acids, aliphatic hydroxy-carboxylic acids and aliphatic alcohols.
2. Preparations for parenteral use having enhanced male sexual hormone action, obtained by combining testosterone with higher aliphatic Preparations for parenteral use having encarboxylic acids. hanced male sexual hormone action, obtained 3. Preparations for parenteral use having enby combining testosterone with higher aliphatic hanced male sexual hormone action, obtained alcohols.
5 by combining testosterone with higher aliphatic KARL MIESCHER.
hydroxy-carboxylic acids. ALBERT WE'ITS'I'EIN.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH2173337X | 1936-02-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2173337A true US2173337A (en) | 1939-09-19 |
Family
ID=4567826
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US125122A Expired - Lifetime US2173337A (en) | 1936-02-25 | 1937-02-10 | Preparation having enhanced sexual hormone action and process of making same |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2173337A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2831873A (en) * | 1954-10-13 | 1958-04-22 | Pfizer & Co C | Testosterone 4, 4-dimethyl pentanoate |
| US2842567A (en) * | 1953-05-09 | 1958-07-08 | Boehringer & Soehne Gmbh | Therapeutically valuable esters of alcohols and ketoalcohols of the steroid series and process of preparing same |
| DE973506C (en) * | 1953-10-02 | 1960-03-10 | Schering Ag | Process for the production of highly concentrated solutions of steroids |
-
1937
- 1937-02-10 US US125122A patent/US2173337A/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2842567A (en) * | 1953-05-09 | 1958-07-08 | Boehringer & Soehne Gmbh | Therapeutically valuable esters of alcohols and ketoalcohols of the steroid series and process of preparing same |
| DE973506C (en) * | 1953-10-02 | 1960-03-10 | Schering Ag | Process for the production of highly concentrated solutions of steroids |
| US2831873A (en) * | 1954-10-13 | 1958-04-22 | Pfizer & Co C | Testosterone 4, 4-dimethyl pentanoate |
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