US2998423A - Esters of 19-nortestosterone - Google Patents
Esters of 19-nortestosterone Download PDFInfo
- Publication number
- US2998423A US2998423A US790357A US79035759A US2998423A US 2998423 A US2998423 A US 2998423A US 790357 A US790357 A US 790357A US 79035759 A US79035759 A US 79035759A US 2998423 A US2998423 A US 2998423A
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- United States
- Prior art keywords
- nortestosterone
- effect
- esters
- anabolic
- compounds
- 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
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- 229960004719 nandrolone Drugs 0.000 title claims description 25
- 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 title claims description 15
- 150000002148 esters Chemical class 0.000 title description 11
- 239000002253 acid Substances 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
- 230000001548 androgenic effect Effects 0.000 description 14
- 230000001195 anabolic effect Effects 0.000 description 13
- 235000015489 Emblica officinalis Nutrition 0.000 description 11
- 240000009120 Phyllanthus emblica Species 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 239000000243 solution Substances 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 230000002349 favourable effect Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- -1 octene carboxylate Chemical class 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 229940070765 laurate Drugs 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229940049964 oleate Drugs 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 230000002035 prolonged effect Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 229960003604 testosterone Drugs 0.000 description 3
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N alpha-tetradecene Natural products CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 229940069096 dodecene Drugs 0.000 description 2
- 235000013372 meat Nutrition 0.000 description 2
- 229940105132 myristate Drugs 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 210000001625 seminal vesicle Anatomy 0.000 description 2
- 229940095068 tetradecene Drugs 0.000 description 2
- 229940075466 undecylenate Drugs 0.000 description 2
- 201000010653 vesiculitis Diseases 0.000 description 2
- 230000001792 virilizing effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 206010011985 Decubitus ulcer Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 206010003549 asthenia Diseases 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- NWADXBLMWHFGGU-UHFFFAOYSA-N dodecanoic anhydride Chemical compound CCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCC NWADXBLMWHFGGU-UHFFFAOYSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000011164 ossification Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- MZFGYVZYLMNXGL-UHFFFAOYSA-N undec-10-enoyl chloride Chemical compound ClC(=O)CCCCCCCCC=C MZFGYVZYLMNXGL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
Definitions
- the compounds according to the invention are 17-esters of 1'9-nortestosterone and saturated and unsaturated ali phatic carboxylic acids having 9-4 8 carbon atoms.
- Esters of l9-nortestosterone are descrlbed, the ana-
- the difference in weight of the musculi levator ani li nd androgenic i y of which are y f (AMLA) then is a measure for the anabolic and thatof ably d-
- AMLA musculi levator ani li nd androgenic i y of which are y f
- ASV seminal vesicles
- AMLA/ ASP is a measure for the rela- With 9 t0 Flght carbon atoms aromatlo'allp hatlo tion between anabolic and androgenic activity.
- th1s relation is as great as i i i esters f of '19 g z ig i possible. This relation should not only be favourable. at figgfgl b zzg ggi ig i g p g 55 g g a g a certain time after administration, but should maintain anabolic and androgenic activity is the most favouri faqourable value as long substance m able.
- esters 1 It is an object of this invention to provide new esters 1
- the following results were obtained (each figure is of l9-nortestosterone the relation of the anabolic and the the result of an experiment performed with 8 rats weigh: androgenic effect of which is more favourable than in the mg about grams when the experiment started); nor-TPP and which have a duration of action which is The treatment consists of a single administration of substantially longer than that of the nor-TPP.. 50 1 mg. ofthe compound in question.
- the present compounds do not only have favourable efiects in the animal experiment, but also on clinical application. It has appeared for example in nitrogen balance experiments in men that in a certain case the protein-saving effect of the nor-TPP which is applied on a very large scale amounted to about g. daily during the first 15 days after injection, whereas this with for example the nortestosterone undecylenate and -decanoate amounted to about 25 g. daily after administration of an equal dose. This larger effect, added to the much more prolonged effect renders the present compounds very valuable for clinical application.
- acids with more than one double bond may be considered for the present process, as well as acids with a triple bond.
- start is preferably made from the acid chloride of the acid in question.
- Example I (a) 1 g. of 19-nortestosterone is dissolved in 3 ml. of dry pyridine, after which the resulting solution is cooled to 20 C. A solution of 1. g. of undecylenic acid chloride in 3 ml. of dry benzene is added to the cooled solution. The mixture is maintained at 15 C. for 16 hours and then poured into ice water. The aqueous liquid is extracted with benzene, the benzene solution is washed with respt. 1 N sodium hydroxide solution, 2 N hydrochloric acid and with water till neutral reaction.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Description
United State Pa q o 2,998,423 ESTERS OF 19-NORTESTOSTERONE Erik 'Duyven De Wit, Oss, and Gerhard Anthony Overbeek, Nijmegen, Netherlands, assignors to Organon ice The compounds according to the invention are 17-esters of 1'9-nortestosterone and saturated and unsaturated ali phatic carboxylic acids having 9-4 8 carbon atoms.
These compounds can be prepared by converting hm West range,NJ a coulomb-on of New Jersey l9-nortestosterone into said esters in a manner known No brawing. Filed Fb. 2, 1959, Ser. No. 790,357 P so for ester a i n, for example y reacting Claims priority, application Netherlands Feb. 25, 1958 19-nortestosterone dissolved in a suitable solvent with the 4 Claims. (Cl. 260-4974) acid chloride of the desired acid or with the anhydride of said acid. V The present invention pertains to new esters of 19-n0r: 10 Th t ti f th fi t f compounds n th rel tion testosterone. between anabolic and androgenic activity is mostly car It is known that testosterone and esters thereof have an ied out b means f tests on castrated rats, i hi h. anabolic effect in addition 10 a andmganic effect some time after the administration of the compound to- Owing to their anabolic activity these compounds have be tested the weights of the musculus-levator ani andi been applied for example in the treatment of cancer of of h Seminal vesicles i determined, the breast, in which, however, the virilizing efiect is most At the same time the weights of these organs areundesirable. One hasv therefore long been seekingtor d ter ined of rats of the same age to which the com"- compounds that do have an anabolic but y a sllght pound in question has not been administered but which virilizing effect. have been treated further in quite the same manner. Esters of l9-nortestosterone are descrlbed, the ana- The difference in weight of the musculi levator ani li nd androgenic i y of which are y f (AMLA) then is a measure for the anabolic and thatof ably d- These arethe esters of l9-nortestostero ne the seminal vesicles (ASV) for the androgenic activity; and alipha'ilc cyclo-allphatlc-allphatlc ay a aclqs So the relation AMLA/ ASP is a measure for the rela- With 9 t0 Flght carbon atoms aromatlo'allp hatlo tion between anabolic and androgenic activity. g j t of whlch the ahphatlc Part contams 2 With substances which are destined for clinical apor car onaoms.
pl1cat1on it is desirablerthat th1s relation is as great as i i i esters f of '19 g z ig i possible. This relation should not only be favourable. at figgfgl b zzg ggi ig i g p g 55 g g a g a certain time after administration, but should maintain anabolic and androgenic activity is the most favouri faqourable value as long substance m able. Consequently this compound is applied in a very ex erts some S0 it may not be W t large number of cases, of which may be mentioned by after in ection the substance has a good anabohc effect way of example cancer of the breast, osteoporosis, and a Shght "mhzmg efiect, Whllo thls would be th V decubitus, retarded growth, asthenia, osteogenesis imother Way about after f 875511111916 a Weekperfecta and for which further reference may be made o above f 111 Whloh AMLA/ASV to the very extensive medical literature on this compound. mllled, rs v ry Suitable for testing anabolic compounds;
Although in most of the cases excellent results are obbficausa has pp that there is a very good'correlatained with this known compound, the need remains for 11011 between the effect 0f the substances in test and anabolically acting compounds having a more prolonged 40 on clinical application. I effect than the l9-nortestosterone fl-phenylpropionate I The present compounds have been tested according to (hereinafter indicated by nor-TPP). In addition one the above method and compared with the compound is searching for compounds in which the relation between S0 far known to be the compound having the most favour-1 the anabolic and the androgenic effect is even more able relation between anabolic and androgenic efrect, viz.- favourable than in the nor-TPP'. the nor-TPP. I 7
It is an object of this invention to provide new esters 1 The following results were obtained (each figure is of l9-nortestosterone the relation of the anabolic and the the result of an experiment performed with 8 rats weigh: androgenic effect of which is more favourable than in the mg about grams when the experiment started); nor-TPP and which have a duration of action which is The treatment consists of a single administration of substantially longer than that of the nor-TPP.. 50 1 mg. ofthe compound in question.
Effect after2 weeks Effect after 4 Weeks Effect after 6 weeks Treatment AMLA ABV AMLA/ AMLA ASV AMLA/ AMLA ASV AMLAI. Asv ASV ASV q nor-TPP 21.4 9.7 '22 5.3 5.4 7.0 7.1 19-n0rtest.unde- 4 cylenate 25. 4 5. 0 5. 3 as. e 5. 0 7. 7 a2. 1 5. 5 5. o IQ-nortest. octene carboxylate 21.2 5.9 4.5 35.2 5.4 5.7 24.3 4.8 5.1 19-nortest. dodecene earboxylate 22. 8 6. 0 3. 8 30. 3 5.1 5. 9 28. 6 3. 2 9.0 IQ-nortest. tetradecene carboxylate 22.5 4.5 4.9 22.4 4.2 5.3 20.1 3.7 5.4 19-nortest oleate 15. 8 3. 5 4. s 24. 2 4. 0 6. 0 25. 7 4. 1 s. a 19-nortest. decan ate 25.0 2. 7 9. 2 e2. 7 5. 5 11.4 50 5. s 7. a 19-nortest. laurate.-- 23. 2 2. 7 8. 6 5. s 12 5s 5. 9 s. 4 19-nortest. myria- 19. 4 2. 2 8. 8 42 4. 2 1o 43. 7 4.1 10. 7 19-nortest, palmt- It follows from this table that after 4 weeks the effect of the nor-TPP has ceased practically entirely.
As with this compound AMLA is only very slight after the said period of time, the statement of the value of AMLA/ASV has no purpose here (theoretically both ASV and AMLA would have to be nil if there is no efiect at all). It also appears from the table that the present compounds do not only have a larger proteinsaving effect but also a slighter androgenic effect, while even after 6 weeks a pronounced eifect is present.
That is the present compounds the relation between the anabolic and the androgenic effect would be so favourable could by no means be anticipated, because it is known that on esterification of testosterone with some of the acids in question the androgenic effect increases very strongly. It was not to be expected that with nor-testosterone the very anabolic effect and not the androgenic effect should be amplified to such a large extent.
The present compounds do not only have favourable efiects in the animal experiment, but also on clinical application. It has appeared for example in nitrogen balance experiments in men that in a certain case the protein-saving effect of the nor-TPP which is applied on a very large scale amounted to about g. daily during the first 15 days after injection, whereas this with for example the nortestosterone undecylenate and -decanoate amounted to about 25 g. daily after administration of an equal dose. This larger effect, added to the much more prolonged effect renders the present compounds very valuable for clinical application.
The initial effect of the 19-nortestosterone oleate and -palmitate is somewhat smaller than that of the other compounds; against this is the more prolonged efiect, as a result of which this compound becomes of great importance for veterinary application, because for example by a single injection in young pigs the protein formation can be promoted to a very great extent at the expense of the deposit of fat, as a result of which an improved meat is obtained in a shorter time. Any unpleasant taste of the meat, as is the case after injection of androgenic substances, need not be feared, because the androgenic effect of these compounds is negligible.
In addition to the acids with one double bond also acids with more than one double bond may be considered for the present process, as well as acids with a triple bond.
In the process according to the invention start is preferably made from the acid chloride of the acid in question.
The following examples illustrate the process.
Example I (a) 1 g. of 19-nortestosterone is dissolved in 3 ml. of dry pyridine, after which the resulting solution is cooled to 20 C. A solution of 1. g. of undecylenic acid chloride in 3 ml. of dry benzene is added to the cooled solution. The mixture is maintained at 15 C. for 16 hours and then poured into ice water. The aqueous liquid is extracted with benzene, the benzene solution is washed with respt. 1 N sodium hydroxide solution, 2 N hydrochloric acid and with water till neutral reaction.
Then the solution is dried on sodium sulphate, filtered, and evaporated to dryness. The residue, 1.63 g. is dissolved in hexane, this solution is filtered over 30 g. of neutral aluminium oxide, and evaporated to dryness. On paper chromatographic investigation it turned out that the obtained 19-nortestosterone l7-undecylenate which at room temperature is an oil consists of a single compound. [oz] =+39.6 (in chloroform). E 15,600 (in ethanol).
(b) In the same manner as mentioned sub (a) the octene carboxylic ester of 19-nortestosterone is prepared in a yield of 88%. E ,,=15,900 (in ethanol).
(0) In the same manner as mentioned sub (a) the dodecene carboxylic ester of 19-nortestosterone is prepared in a yield of 83%. E ,,=16,200 (in ethanol).
(d) In the same manner as mentioned sub (a) the tetradecene carboxylic ester of 19-nortestosterone is prepared in a yield of z39,.=15,600 (in ethanol).
(e) In the same manner as mentioned sub (a) the oleate of 19-nortestosterone is prepared in a yield of 87%. E ,,=l5,400 (in ethanol).
(7) In the same manner as mentioned sub (a) the clecanoate of 19-nortestosterone is prepared in a nearly quantitative yield. The ester is an oil at room temperature. E ,,=l6,000 (in ethanol).
(g) In the same manner as mentioned sub (a) the myristate of l9-nortestosterone is prepared in a yield of 95%. E 15,900 (in ethanol).
(h) In the same manner as mentioned sub (a) the palmitate of 19-nortestosterone is prepared in a yield of 90%. [a] =+32.9 (in chloroform), E ,,=l5,300 (in ethanol), M.P. 53-56 C.
Example ll 1 g. of l9-nortestosterone and 2 g. of lauric anhydride are dissolved in 20 ml. of dry pyridine. The mixture is refluxed for 4 hours. Then 2 ml. of water are added and refluxing is continued for some more hours in order to decompose the excess of anhydride. Then the mixture is evaporated to dryness, the residue is taken up in benzene, after which this benzene solution is treated in the manner of Example I. In this manner the 19-nortestosterone-17-laurate is obtained in a yield. [a] ==+37.4 (in chloroform); E ,,=l5,900; M.P. 45-46" C.
What we claim is:
1. l9-nortestosterone 17-esters of saturated straight chain aliphatic carboxylic acids containing from 10 to 14 carbon atoms.
2. l9-nortestosterone 17-decanoate.
3. 19-nortestosterone17-laurate.
4. -19-nortestosterone 17-myristate.
References Cited in the file of this patent UNITED STATES PATENTS 2,308,834 Ruzicka et a1. Jan. 19, 1943 2,756,244 Djerassi et a1. July 24, 1956 2,831,873 Pinson et a1 Apr. 22, 1958 2,868,809 Donia et a1. Jan. 13, 1959 2,904,562 Diczfalusy et al. Sept. 15, 1959 2,964,537 Engelfried et al. Dec. 13, 1960
Claims (1)
1. 19-NORTESTOSTERONE 17-ESTERS OF SATURATED STRAIGHT CHAIN ALIPHATIC CARNOXYLIC ACIDS CONTAINING FROM 10 TO 14 CARBON ATOMS.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL2998423X | 1958-02-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2998423A true US2998423A (en) | 1961-08-29 |
Family
ID=19876659
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US790357A Expired - Lifetime US2998423A (en) | 1958-02-25 | 1959-02-02 | Esters of 19-nortestosterone |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2998423A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3506763A (en) * | 1965-12-20 | 1970-04-14 | Squibb & Sons Inc | Method of promoting growth of animals with testololactones |
| US4083973A (en) * | 1975-08-27 | 1978-04-11 | Akzona Incorporated | Pharmaceutical preparation adapted for oral administration |
| US5208032A (en) * | 1988-07-15 | 1993-05-04 | Rutgers, The State University Of New Jersey | Increasing the growth of turkeys using implant of 19-nortestosterone |
| US20040058898A1 (en) * | 2002-09-25 | 2004-03-25 | Chang-Eun Jung | Pharmaceutical composition for alleviating the violence of a mammal comprising nortestosterone derivatives |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2308834A (en) * | 1936-06-15 | 1943-01-19 | Ciba Pharm Prod Inc | Polynuclear cyclic oxyketones and derivatives thereof and process of making same |
| US2756244A (en) * | 1953-07-11 | 1956-07-24 | Syntex Sa | 19-norandrostanolones and process |
| US2831873A (en) * | 1954-10-13 | 1958-04-22 | Pfizer & Co C | Testosterone 4, 4-dimethyl pentanoate |
| US2868809A (en) * | 1954-08-12 | 1959-01-13 | Upjohn Co | 19-nortestosterone phenyl alkanoates |
| US2904562A (en) * | 1958-01-20 | 1959-09-15 | Leo Ab | Esters of testosterone and 19-nortestosterone and method for the production thereof |
| US2964537A (en) * | 1956-06-16 | 1960-12-13 | Schering Ag | Therapeutically valuable carboxylic acid esters of 17-alkyl-19-nor-testosterone |
-
1959
- 1959-02-02 US US790357A patent/US2998423A/en not_active Expired - Lifetime
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2308834A (en) * | 1936-06-15 | 1943-01-19 | Ciba Pharm Prod Inc | Polynuclear cyclic oxyketones and derivatives thereof and process of making same |
| US2756244A (en) * | 1953-07-11 | 1956-07-24 | Syntex Sa | 19-norandrostanolones and process |
| US2868809A (en) * | 1954-08-12 | 1959-01-13 | Upjohn Co | 19-nortestosterone phenyl alkanoates |
| US2831873A (en) * | 1954-10-13 | 1958-04-22 | Pfizer & Co C | Testosterone 4, 4-dimethyl pentanoate |
| US2964537A (en) * | 1956-06-16 | 1960-12-13 | Schering Ag | Therapeutically valuable carboxylic acid esters of 17-alkyl-19-nor-testosterone |
| US2904562A (en) * | 1958-01-20 | 1959-09-15 | Leo Ab | Esters of testosterone and 19-nortestosterone and method for the production thereof |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3506763A (en) * | 1965-12-20 | 1970-04-14 | Squibb & Sons Inc | Method of promoting growth of animals with testololactones |
| US4083973A (en) * | 1975-08-27 | 1978-04-11 | Akzona Incorporated | Pharmaceutical preparation adapted for oral administration |
| US5208032A (en) * | 1988-07-15 | 1993-05-04 | Rutgers, The State University Of New Jersey | Increasing the growth of turkeys using implant of 19-nortestosterone |
| US20040058898A1 (en) * | 2002-09-25 | 2004-03-25 | Chang-Eun Jung | Pharmaceutical composition for alleviating the violence of a mammal comprising nortestosterone derivatives |
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