DE1223373B - Process for the production of testosterone cyclohexyl carbonate - Google Patents
Process for the production of testosterone cyclohexyl carbonateInfo
- Publication number
- DE1223373B DE1223373B DEL40240A DEL0040240A DE1223373B DE 1223373 B DE1223373 B DE 1223373B DE L40240 A DEL40240 A DE L40240A DE L0040240 A DEL0040240 A DE L0040240A DE 1223373 B DE1223373 B DE 1223373B
- Authority
- DE
- Germany
- Prior art keywords
- testosterone
- cyclohexyl carbonate
- carbonate
- production
- cyclohexyl
- 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.)
- Pending
Links
- 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 title claims description 44
- 229960003604 testosterone Drugs 0.000 title claims description 22
- FRJZOYQRAJDROR-UHFFFAOYSA-N cyclohexyl hydrogen carbonate Chemical compound OC(=O)OC1CCCCC1 FRJZOYQRAJDROR-UHFFFAOYSA-N 0.000 title claims description 17
- 238000000034 method Methods 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- IWVJLGPDBXCTDA-UHFFFAOYSA-N cyclohexyl carbonochloridate Chemical compound ClC(=O)OC1CCCCC1 IWVJLGPDBXCTDA-UHFFFAOYSA-N 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 241000700159 Rattus Species 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- YKNXICSCSYLTHK-IXKNJLPQSA-N [(8r,9s,10r,13s,14s,17s)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] cyclohexanecarboxylate Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(CCC(=O)C=C4CC3)C)CC[C@@]21C)C(=O)C1CCCCC1 YKNXICSCSYLTHK-IXKNJLPQSA-N 0.000 description 3
- 230000001195 anabolic effect Effects 0.000 description 3
- 230000001548 androgenic effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 210000003734 kidney Anatomy 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- -1 steroid esters Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- PDMMFKSKQVNJMI-BLQWBTBKSA-N Testosterone propionate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CC)[C@@]1(C)CC2 PDMMFKSKQVNJMI-BLQWBTBKSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000000956 myotropic effect Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229960001712 testosterone propionate Drugs 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 238000011047 acute toxicity test Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003098 androgen Substances 0.000 description 1
- 150000001441 androstanes Chemical class 0.000 description 1
- 238000011888 autopsy Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002159 estradiols Chemical class 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- GECNIOWBEXHZNM-UHFFFAOYSA-N hexyl hydrogen carbonate Chemical compound CCCCCCOC(O)=O GECNIOWBEXHZNM-UHFFFAOYSA-N 0.000 description 1
- BGMIRDHBNWQSGE-UHFFFAOYSA-N hypochlorous acid;pyridine Chemical compound ClO.C1=CC=NC=C1 BGMIRDHBNWQSGE-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 231100000566 intoxication Toxicity 0.000 description 1
- 230000035987 intoxication Effects 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000268 renotropic effect Effects 0.000 description 1
- 210000001625 seminal vesicle Anatomy 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 201000010653 vesiculitis Diseases 0.000 description 1
- 238000005406 washing Methods 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Description
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
AUSLEGESCHRIFTEDITORIAL
Int. CL:Int. CL:
C07cC07c
Nummer: 1 223 373Number: 1 223 373
Aktenzeichen: L 40240IV b/12 οFile number: L 40240IV b / 12 ο
Anmeldetag: 17. Oktober 1961Filing date: October 17, 1961
Auslegetag: 25. August 1966Opening day: August 25, 1966
Es ist schon eine beträchtliche Anzahl von Steroidestern bekannt, insbesondere 17- oder 3-Ester der östradiolreihe, 17-Ester der Androstanreihe und 21-Ester der Corticosteroidreihe, wobei die Versterung im allgemeinen den Zweck hatte, die Steroid-Verbindungen löslich zu machen oder ihnen eine verlängerte Wirkungsdauer zu verleihen.A considerable number of steroid esters are already known, in particular 17 or 3 esters of estradiol series, 17-ester of the androstane series and 21-ester of the corticosteroid series, with the esterification The general purpose was to make the steroid compounds soluble or to give them a solubility to give extended duration of action.
Die Erfindung betrifft ein Verfahren zur Herstellung eines neuen Steroidesters, und zwar des Testosteroncyclohexylcarbonats der FormelThe invention relates to a method of manufacture of a new steroid ester, namely the testosterone cyclohexyl carbonate of the formula
worin St den Testosteronrest bedeutet.where St is the testosterone residue.
Die neue Verbindung zeichnet sich besonders durch eine ausgezeichnete Löslichkeit in öligen oder den sonst üblichen organischen Lösungsmitteln aus, verbunden mit einer verzögerten Wirkung, die es gestattet, daß die Verabreichung in größeren Zeitabständen erfolgen kann. Sie kann außerdem als Zwischenprodukt für Steroidsynthesen dienen.The new compound is particularly characterized by excellent solubility in oily or the otherwise common organic solvents, combined with a delayed effect that allows that the administration can take place at longer time intervals. It can also be used as an intermediate serve for steroid syntheses.
Das erfindungsgemäße Verfahren besteht darin, daß man Testosteron mit Chlorameisensäurecyclohexylester in basischem Milieu in an sich bekannter Weise umsetzt und das Testosteroncyclohexylcarbonat nach bekannten Methoden isoliert.The inventive method consists in that testosterone with cyclohexyl chloroformate converts in a basic medium in a manner known per se and the testosterone cyclohexyl carbonate after known methods isolated.
Es ist vorteilhaft, die Veresterung in einer tertiären Base, wie Pyridin, vorzunehmen.It is advantageous to carry out the esterification in a tertiary base such as pyridine.
Das folgende Beispiel dient der näheren Erläuterung des erfindungsgemäßen Verfahrens. Die Temperatuen sind in Celsiusgraden angegeben.The following example serves to explain the process according to the invention in more detail. The temperatures are given in degrees Celsius.
Verfahren zur Herstellung von
TestosteroncyclohexylcarbonatProcess for the production of
Testosterone cyclohexyl carbonate
Herstellung von TestosteroncyclohexylcarbonatManufacture of testosterone cyclohexyl carbonate
Man löst 10 g Testosteron in 50 ecm wasserfreiem Pyridin, kühlt auf +10° ab und trägt unter Rühren
tropfenweise 15 ecm Chlorameisensäurecyclohexylester ein. Das Reaktionsgemisch nimmt zunächst eine
rosa Färbung an und wird dann violett; das Pyridinchlorhydrat fällt aus. Man läßt eine Nacht bei Raumtemperatur
stehen, gießt dann in Eiswasser, rührt und extrahiert mit Äther. Die Extrakte werden nach
dem Waschen mit Salzsäure und mit Wasser über Natriumsulfat getrocknet, dann unter Vakuum zur
Trockne eingedampft. Man erhält einen Rückstand von 17,9 g rohes Testosteroncyclohexylcarbonat, das
man chromatographisch an saurem Aluminiumoxyd reinigt, wobei als Lösungsmittel Cyclohexan verwendet
wird. Man erhält 7,6 g (ungefähr 53 °/0) eines gelben Produkts, das in den üblichen organischen
Lösungsmitteln, wie Alkohol, Äther, Aceton, Benzol, Anmelder:
Roussel-Uclaf, Paris10 g of testosterone are dissolved in 50 ecm of anhydrous pyridine, cooled to + 10 ° and, with stirring, 15 ecm of cyclohexyl chloroformate is added dropwise. The reaction mixture initially takes on a pink color and then turns purple; the pyridine chlorohydrate precipitates. The mixture is left to stand at room temperature for one night, then poured into ice water, stirred and extracted with ether. After washing with hydrochloric acid and with water, the extracts are dried over sodium sulfate and then evaporated to dryness in vacuo. A residue of 17.9 g of crude testosterone cyclohexyl carbonate is obtained, which is purified by chromatography on acidic aluminum oxide, cyclohexane being used as the solvent. This gives 7.6 g (approximately 53 ° / 0) of a yellow product, which in the usual organic solvents such as alcohol, ether, acetone, benzene, Applicant:
Roussel-Uclaf, Paris
Vertreter:Representative:
Dr. F. Zumstein,Dr. F. Zumstein,
Dipl.-Chem. Dr. rer. nat. E. AssmannDipl.-Chem. Dr. rer. nat. E. Assmann
und Dipl.-Chem. Dr. R. Koenigsberger,and Dipl.-Chem. Dr. R. Koenigsberger,
Patentanwälte, München 2, Bräuhausstr. 4Patent Attorneys, Munich 2, Bräuhausstr. 4th
Als Erfinder benannt:Named as inventor:
Andre Allais, Paris;Andre Allais, Paris;
Dr. Jean Meier, Coeuilly-Champigny, SeineDr. Jean Meier, Coeuilly-Champigny, Seine
(Frankreich)(France)
Beanspruchte Priorität:Claimed priority:
Frankreich vom 27. Oktober 1960 (842 375),France of October 27, 1960 (842 375),
vom 28. Dezember 1960 (848 182) ■dated December 28, 1960 (848 182) ■
Chloroform, Cyclohexan und Petroläther, sowie in Olivenöl löslich, jedoch in Wasser unlöslich ist. [«]*> = +80° (c = 0,6%, Äthanol).Chloroform, cyclohexane and petroleum ether, as well as soluble in olive oil, but insoluble in water. [«] *> = + 80 ° (c = 0.6%, ethanol).
Analyse: C26H38O4 = 414,56
Berechnet... C 75,32, H 9,24%;
gefunden ... C 75,2, H 9,3%.Analysis: C 26 H 38 O 4 = 414.56
Calculated ... C 75.32, H 9.24%;
found ... C 75.2, H 9.3%.
Die Verbindung wurde in der Literatur bisher noch nicht beschrieben.The compound has not yet been described in the literature.
Pharmakologische VersuchePharmacological experiments
mit Testosteroncyclohexylcarbonatwith testosterone cyclohexyl carbonate
Bestimmung der androgenen undDetermination of androgenic and
anabolischen bzw. myotropen Wirkunganabolic or myotropic effects
Die Versuche wurden nach der Methode von Sakamoto und Mitarbeitern (Proced. Soc. Exp. Biol. Med., 76, 1951, S. 406) durchgeführt. Männliche Ratten, die im Alter von 41Z2 Wochen kastriert worden waren, erhielten im Alter von 7x/2 Wochen eine einmalige subkutane Injektion von Testosteroncyclohexylcarbonat, das vorher in einem öligen Lösungsmittel gelöst worden war. Jede Ratte erhielt eine Dosis von 25 mg. Dann wurden sie zu gestaffeltenThe experiments were carried out according to the method of Sakamoto and co-workers (Proced. Soc. Exp. Biol. Med., 76, 1951, p. 406). Male rats which had been castrated at the age of 4 1 2 weeks received a single subcutaneous injection of testosterone cyclohexyl carbonate which had previously been dissolved in an oily solvent at the age of 7 × / 2 weeks. Each rat received a dose of 25 mg. Then they became staggered
609 657/424609 657/424
Zeitpunkten getötet; nämlich 10, 17, 24 und 31 Tage nach der Injektion. Nach dem Töten wurden die Tiere der Autopsie unterworfen und die interessierenden Organe entnommen, insbesondere die Samenbläschen, um den Androgeneffekt zu studieren, und die Nieren und der Musculus levator ani, um die renotrope und die myotrope Wirkung zu studieren.Times killed; namely 10, 17, 24 and 31 days after the injection. After the killing, the Subjects the animals to the autopsy and removed the organs of interest, especially the Seminal vesicles to study the androgen effect, and the kidneys and levator ani muscle to study the to study renotropic and myotropic effects.
Die erhaltenen Resultate sind in der folgendenThe results obtained are as follows
Tabelle und in zwei vergleichenden Kurven zusammengefaßt. Table and summarized in two comparative curves.
Ratten in
WochenAge of
Rats in
Weeks
Wirkung in
TagenDuration of
Effect in
Days
der Ratten
(g)weight
of rats
(G)
der Samen
bläschen
(mg)weight
the seed
vesicles
(mg)
der
TiereZaM
the
animals
hexylcarbonatTestosterone cyclo-
hexyl carbonate
hexylcarbonatTestosterone cyclo-
hexyl carbonate
hexylcarbonatTestosterone cyclo-
hexyl carbonate
hexylcarbonatTestosterone cyclo-
hexyl carbonate
Erklärung:Explanation:
Gewicht der frischen Niere · 1000 Rf = Fresh kidney weight x 1000 Rf =
Ri =Ri =
Körpergewichtbody weight
Gewicht der trockenen Niere · 1000Weight of dry kidney 1000
Körpergewichtbody weight
IfIf
IsIs
Gewicht des frischen Levator ani · 1000
KörpergewichtWeight of the fresh levator ani 1000
body weight
Gewicht des trockenen Levator ani · 1000
KörpergewichtWeight of dry levator ani 1000
body weight
Man kann beim Prüfen des Resultats feststellen, daß das Testosteroncyclohexylcarbonat einen intensiven und dauerhaften Androgeneffekt und einen bemerkenswerten anabolischen Effekt besitzt.When checking the result, one can see that the testosterone cyclohexyl carbonate has an intense and has a lasting androgenic effect and a remarkable anabolic effect.
Bestimmung der akuten ToxizitätDetermination of acute toxicity
Der Versuch über die akute Toxizität wurde an Mäusen vom Stamm Rockland durchgeführt, die zwischen 18 und 22 g wogen. Das Testosteroncyclohexylcarbonat wurde in einem öligen Lösungsmittel gelöst, und es wurde zehn Mäusen je eine Dosis von 250 mg/kg subkutan injiziert.The acute toxicity test was carried out on mice from the Rockland strain, which weighed between 18 and 22 g. The testosterone cyclohexyl carbonate was in an oily solvent dissolved, and ten mice were each injected with a dose of 250 mg / kg subcutaneously.
Die Tiere wurden nach der Injektion 1 Woche lang unter Beobachtung gehalten.The animals were kept under observation for 1 week after the injection.
Es wurden weder Intoxikationssymptome noch eine Mortalität im Verlauf dieser Periode festgestellt. Die Verbindung ist also nicht einmal bei einer Dosis von 250 mg/kg toxisch.No symptoms of intoxication or mortality were noted during this period. the So compound is not toxic even at a dose of 250 mg / kg.
Der Vergleich der erfindungsgemäß herstellbaren Substanz Testosteroncyclohexylcarbonat mit den bekannten Substanzen Testosteronhexahydrobenzoat und Testosteronpropionat hat gezeigt, daß Testosteroncyclohexylcarbonat seine maximale Wirkung nach Injektion noch nach 31 Tagen zeigt, während die Verabreichung von Testosteronhexahydrobenzoat eine geringere maximale Wirkung zeigt, die auch schon nach 3 Wochen abnimmt, und die Wirkung von Testosteronpropionat noch geringer ist als die von Testosteronhexahydrobenzoat (vgl. C. R. F e y e 1, Soc. Biol., 1954, Bd. 148, S. 1196).The comparison of the substance testosterone cyclohexyl carbonate which can be prepared according to the invention with the known ones Substances testosterone hexahydrobenzoate and testosterone propionate have shown that testosterone cyclohexyl carbonate Its maximum effect after injection still shows after 31 days, while the administration of testosterone hexahydrobenzoate one shows lower maximum effect, which also decreases after 3 weeks, and the effect of Testosterone propionate is even lower than that of testosterone hexahydrobenzoate (cf. C. R. F e y e 1, Soc. Biol., 1954, Vol. 148, p. 1196).
Claims (2)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1223373X | 1960-10-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1223373B true DE1223373B (en) | 1966-08-25 |
Family
ID=9677345
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEL40240A Pending DE1223373B (en) | 1960-10-27 | 1961-10-17 | Process for the production of testosterone cyclohexyl carbonate |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1223373B (en) |
-
1961
- 1961-10-17 DE DEL40240A patent/DE1223373B/en active Pending
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