DE3339295A1 - 4-Hydroxy- and 4-acyloxy-4-androstene-3,17-diones for use in the prophylaxis and therapy of prostate hyperplasia and compositions containing these for such a use - Google Patents
4-Hydroxy- and 4-acyloxy-4-androstene-3,17-diones for use in the prophylaxis and therapy of prostate hyperplasia and compositions containing these for such a useInfo
- Publication number
- DE3339295A1 DE3339295A1 DE19833339295 DE3339295A DE3339295A1 DE 3339295 A1 DE3339295 A1 DE 3339295A1 DE 19833339295 DE19833339295 DE 19833339295 DE 3339295 A DE3339295 A DE 3339295A DE 3339295 A1 DE3339295 A1 DE 3339295A1
- Authority
- DE
- Germany
- Prior art keywords
- androstene
- hydroxy
- diones
- acyloxy
- therapy
- 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.)
- Granted
Links
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
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
Abstract
Description
4-Hydroxy- und 4-Acyloxy-4-androsten-3,17-dione4-hydroxy- and 4-acyloxy-4-androstene-3,17-diones
zur Verwendung bei der Prophylaxe und Therapie der Prostatahyperplasie und diese enthaltende Mittel für derartige Verwendung Die Erfindung betrifft 4-Hydroxy- und 4-Acyloxy-4-androsten-3X17-dione zur Verwendung bei der Prophylaxe und Therapie der Prostatahyperplasie und diese enthaltende Mittel für derartige Verwendung.for use in the prophylaxis and therapy of prostatic hyperplasia and agents containing them for such use The invention relates to 4-hydroxy and 4-acyloxy-4-androstene-3X17-diones for use in the Prophylaxis and therapy of prostatic hyperplasia and agents containing them for such use.
Die erfindungsgemäß zu verwendenden 4-Hydroxy- und 4=Acyloxy-4-androsten-3,17-dione werden durch folgende allgemeine Formel I gekennzeichnet: worin R ein Wasserstoffatom oder eine 2 bis 12 Kohlenstoffatome enthaltende Acylgruppe darstellt.The 4-hydroxy- and 4-acyloxy-4-androstene-3,17-diones to be used according to the invention are characterized by the following general formula I: wherein R represents a hydrogen atom or an acyl group containing 2 to 12 carbon atoms.
Als Acylgruppen kommen die in der Steroidchemie üblicherweise verwendeten Acylgruppen infrage, insbesondere die Acetyl-, Heptanoyl- und Benzoylgruppe.The acyl groups are those commonly used in steroid chemistry Acyl groups in question, especially the acetyl, heptanoyl and benzoyl groups.
Die Verbindungen der allgemeinen Formel I sind bereits bekannt. Sie werden beschrieben als Aromatasehemmer, die die Umwandlung von 4-Androsten-3,17-dion zu Östrogenen an menschlichen Placentamikrosomen hemmen (Endocrinology 100 (1977) 1684 - 1695 und U.S. Patent 4,235,893). Die Verbindungen können die Entwicklung östrogenabhängiger Brusttumoren bei Ratten unterdrücken.The compounds of general formula I are already known. she are described as aromatase inhibitors that reduce the conversion of 4-androstene-3,17-dione to inhibit estrogens on human placenta microsomes (Endocrinology 100 (1977) 1684-1695 and U.S. Patent 4,235,893). The connections can evolve suppressing estrogen-dependent breast tumors in rats.
Bei der Prostatahyperplasie handelt es sich um eine gutartige Vergrößerung der Prostata, die von der sogenannten "inneren" Prostata ihren Ausgang nimmt. Die Beschwerden sind vor allem auf die auftretenden Obstruktionen der Harnröhre zurückzuführen. Die Blasenentleerung ist erschwert, und es kommt zu Restharnretentionen. Ohne operativen Eingriff kann es zu Harnstoffvergiftungen kommen.Prostatic hyperplasia is a benign enlargement the prostate, which starts from the so-called "inner" prostate. the Symptoms are mainly due to the obstruction of the urethra. It is difficult to empty the bladder and residual urine is retained. Without operational Surgery can lead to urea poisoning.
Bislang ist eine medikamentöse Behandlung dieser sehr häufigen Erkrankung bei älteren Männern kaum möglich.So far, drug treatment of this very common disease is available hardly possible in older men.
Die für diesen Zweck benutzten Phyto-Präparate, wie zum Beispiel ß-Sitosterin, Mischungen aus verschiedenen Pflanzenextrakten und Kombinationen aus Pflanzenextrakten mit dem neurotropen Spasmolytikum Azoniaspirochlorid erwiesen sich in einer einjährigen Studie als unwirksam.The phyto-preparations used for this purpose, such as ß-sitosterol, Mixtures of various plant extracts and combinations of plant extracts with the neurotropic antispasmodic azoniaspirochlorid proved themselves in an annual Study as ineffective.
Zwar empfanden die Patienten unter der Therapie eine Besserung der Miktionssymptomatik, eine Rückbildung der hyperplastischen Prostata wurde jedoch nicht erzielt.It is true that the patients felt an improvement in the therapy Micturition symptoms, however, regression of the hyperplastic prostate was observed not achieved.
Auch Hormone finden Anwendung bei der Behandlung der Prostatahyperplasie; von diesen Substanzen ist insbesondere das Depot-Gestagen Gestonoroncapronat zu nennen.Hormones are also used in the treatment of prostatic hyperplasia; Of these substances, in particular, the depot progestin gestonoroncapronate to name.
Im Vergleich mit den Phyto-Präparaten wird mit Gestonoroncapronat eine bessere Wirkung erzielt. Die vor der Behandlung verlängerte Miktionsdauer wird deutlich verkürzt und der maximale Flowwert (Urinfluß in der Zeiteinheit ) verbessert. Eine deutliche Reduktion der Adenomgröße ist aber auch hier nicht festzustellen.In comparison with the phyto-preparations, Gestonoroncapronat is used achieved a better effect. The urination period extended before treatment becomes significantly shortened and the maximum flow value (urine flow in the unit of time ) improved. A significant reduction in the size of the adenoma cannot be found here either.
In der US-Patentschrift 3,423,507 wird die Behandlung der Prostatahypertrophie mit den gestagen und antiandrogen wirkenden Estern des 6-Chlor-17-hydroxy-1a, 2c:-methylen-pregna-4,6-dien-3,20-dions (Cyproteronestern) beschrieben. Es hat sich jedoch gezeigt, daß auch unter dieser Behandlung nur eine teilweise Rückbildung der Hyperplasie eintritt.The treatment of prostatic hypertrophy is described in US Pat. No. 3,423,507 with the gestagenic and antiandrogenic esters of 6-chloro-17-hydroxy-1a, 2c: -methylene-pregna-4,6-diene-3,20-dione (Cyproterone esters). However, it has been shown that even under this Treatment only partially regresses the hyperplasia.
In der DE-OS 28 17 157 wird zur Prophylaxe und Therapie der Prostatahyperplasie die Verwendung von Antiöstrogenen in Kombination mit antiandrogen wirkenden Substanzen vorgeschlagen. Doch die Anwendung von Antiöstrogenen ist nur in einem bestimmten Dosisbereich möglich, da bei höheren Dosen auch Antiöstrogene agonistisch (als östrogene) wirken.In DE-OS 28 17 157 for prophylaxis and therapy of prostatic hyperplasia the use of anti-estrogens in combination with anti-androgenic substances suggested. However, the use of anti-estrogens is only specific Dose range possible, as anti-estrogens are agonistic (than estrogenic) at higher doses works.
Bez der Prostatahyperplasie handelt es sich um eine gutartige Vergrößerung der Prostata, wobei in wechselndem Ausmaß Interstitium (Stroma) und Epithel beteiligt sind.In relation to prostatic hyperplasia, it is a benign enlargement the prostate, the interstitium (stroma) and epithelium being involved to an alternating extent are.
Als Ursache kann u.a. eine Verschiebung des Östrogen/ Androgen-Verhältnisses zugunsten der Östrogene angesehen werden In verschiedenen Untersuchungen hat sich gezeigt, daß bei älteren Männern die Serumtestosteronkonzentratonen abfallen; gleichzeitig nimmt der Anteil an SHBG (sex hormone binding globuline, spezifisches Transportprotein für Steroide) zu, so daß die biologische Verfügbarkeit an Androgenen noch weiter abnimmt.One of the causes may be a shift in the estrogen / androgen ratio In favor of estrogens are viewed in various studies has been made shown that serum testosterone concentrations drop in older men; simultaneously increases the proportion of SHBG (sex hormone binding globuline, specific transport protein for steroids) too, so that the bioavailability of androgens even continues decreases.
Da sowohl östrogene als auch androgene aktoren bei der Prostatahyperplasie eine Rolle spielen, sind die bisher vorgeschlagenen Hormonbehandlungen nicht zufriedenstellend.As both estrogenic and androgenic actors in prostatic hyperplasia play a role, the hormone treatments proposed so far are unsatisfactory.
Es wurde nun gefunden, daß die 4-Hydroxy- und 4-Acyloxy-4-androsten-3,17-dione der allgemeinen Formel I die Stimulation des Prostatagewebes unterbinden. Es kommt zu einer Rückbildung der Drüse und zur Besserung der Miktionsbeschwerden.It has now been found that the 4-hydroxy- and 4-acyloxy-4-androstene-3,17-diones of the general formula I prevent the stimulation of the prostate tissue. It is coming to a regression of the gland and to the improvement of the urination problems.
Es werden täglich 20 mg bis 400 mg, vorzugsweise 50 mg bis 250 mg einer Verbindung der allgemeinen Formel I angewendet.20 mg to 400 mg, preferably 50 mg to 250 mg, are used daily a compound of the general formula I is used.
Der Wirkstoff kann mit den in der galenischen Pharmazie üblichen Zusätzen, Trägersubstanzen und/oder Geschmackskorrigentien nach an sich bekannten Methoden zu den üblichen Applikationsformen verarbeitet werden.The active ingredient can be mixed with the additives customary in galenic pharmacy, Carrier substances and / or taste corrections according to methods known per se processed into the usual forms of application.
Für die bevorzugte orale Applikation kommen insbesondere Tabletten, Dragees, Kapseln, Pillen, Suspensionen oder Lösungen infrage.For the preferred oral administration, tablets are particularly suitable, Dragees, capsules, pills, suspensions or solutions in question.
Für die parenterale, insbesondere intramuskulare Applikation sind ölige Lösungen, wie zum Beispiel Sesamöl-oder Rizinusöllösungen, geeignet. Zur Erhöhung der Löslichkeit können Lösungsvermittler, wie zum Beispiel Benzylbenzoat oder Benzylalkohol, zugesetzt werden.For parenteral, especially intramuscular, administration oily solutions, such as, for example, sesame oil or castor oil solutions, are suitable. To increase solubility promoters, such as benzyl benzoate or benzyl alcohol, can be added.
Die wie oben angegeben formulierten Arzneimittel enthalten für die orale Applikation vorzugsweise 10 mg bis 250 mg und für die parenterale Applikation vorzugsweise 20 mg bis 200 mg 4-Hydroxy-4-androsten-3,17-dion oder einen 4-Carbonsäureester von 4-Hydroxy-4-androsten-3,17-dion.The medicinal products formulated as above contain for the oral administration preferably 10 mg to 250 mg and for parenteral administration preferably 20 mg to 200 mg of 4-hydroxy-4-androstened-3,17-dione or a 4-carboxylic acid ester of 4-hydroxy-4-androstene-3,17-dione.
Zusan-ensetzung von Tabletten Beispiel 1 20,0 mg 4-Hydroxy-4-androsten-3, 17-dion 130,5 mg Lactose 69,5 mg Maisstärke 2,5 mg Poly-N-Vinylpyrrolidon 25 2,0 mg Aerosil °t5 mg Magnesiumstearat 225,0 mg Gesamtgewicht der Tablette1 die in üblicher -------- Weise auf einer Tablettenpresse hergestellt wird.Composition of tablets Example 1 20.0 mg of 4-hydroxy-4-androstene-3, 17-dione 130.5 mg lactose 69.5 mg corn starch 2.5 mg poly-N-vinylpyrrolidone 25 2.0 mg Aerosil ° t5 mg magnesium stearate 225.0 mg total weight of the tablet1 in the usual -------- way is made on a tablet press.
Beispiel 2 50,0 mg 4-Hydroxy-4-androsten-3,17-dion 115,5 mg Lactose mg Maisstärke 2,5 mg Poly-N-Vinylpyrrolidon 25 2,0 mg Aerosil 0,5 mg Magnesiumstearat 225,0 mg Gesamtgewicht der Tablette, die in üblicher Weise Weise auf einer Tablettenpresse hergestellt wird.Example 2 50.0 mg of 4-hydroxy-4-androstened-3,17-dione 115.5 mg of lactose mg corn starch 2.5 mg poly-N-vinylpyrrolidone 25 2.0 mg Aerosil 0.5 mg magnesium stearate 225.0 mg total weight of the tablet, taken in the usual way on a tablet press will be produced.
Beispiel 3 50,0 mg 4-Acetoxy-4-androsten-3,17-dion 115,5 mg Lactose 54,5 mg Maisstärke 2,5 mg Poly-N-Vinylpyrrolidon 25 2,0 mg Aerosil 0,5 mg Magnesiumstearat 225,0 mg Gesamtgewicht der Tablette, die in üblicher -'-'----- Weise auf einer Tablettenpresse hergestellt wird.Example 3 50.0 mg of 4-acetoxy-4-androstene-3,17-dione 115.5 mg of lactose 54.5 mg corn starch 2.5 mg poly-N-vinylpyrrolidone 25 2.0 mg Aerosil 0.5 mg magnesium stearate 225.0 mg total weight of the tablet, in the usual -'-'----- way on a tablet press will be produced.
Beispiel 4 Zusammensetzung einer öligen Lösung 50,0 mg 4-Acetoxy-4-androsten-3,17-dion 378,4 mg Rizinusöl 643,6 mg Benzylbenzoat 1072,0 mg = 1 ml Lösung Die Lösung wird in eine Ampulle gefüllt und sterilisiert.Example 4 Composition of an oily solution 50.0 mg of 4-acetoxy-4-androstene-3,17-dione 378.4 mg castor oil 643.6 mg benzyl benzoate 1072.0 mg = 1 ml solution The solution becomes filled into an ampoule and sterilized.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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DE19833339295 DE3339295A1 (en) | 1982-11-15 | 1983-10-27 | 4-Hydroxy- and 4-acyloxy-4-androstene-3,17-diones for use in the prophylaxis and therapy of prostate hyperplasia and compositions containing these for such a use |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE3242465 | 1982-11-15 | ||
DE19833339295 DE3339295A1 (en) | 1982-11-15 | 1983-10-27 | 4-Hydroxy- and 4-acyloxy-4-androstene-3,17-diones for use in the prophylaxis and therapy of prostate hyperplasia and compositions containing these for such a use |
Publications (2)
Publication Number | Publication Date |
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DE3339295A1 true DE3339295A1 (en) | 1984-05-17 |
DE3339295C2 DE3339295C2 (en) | 1992-05-27 |
Family
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DE19833339295 Granted DE3339295A1 (en) | 1982-11-15 | 1983-10-27 | 4-Hydroxy- and 4-acyloxy-4-androstene-3,17-diones for use in the prophylaxis and therapy of prostate hyperplasia and compositions containing these for such a use |
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Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0181287A2 (en) * | 1984-11-06 | 1986-05-14 | Ciba-Geigy Ag | Dry substances and stable suspensions |
WO1991000733A1 (en) * | 1989-07-07 | 1991-01-24 | Endorecherche Inc. | Method of treatment of androgen-related diseases |
WO1991000732A1 (en) * | 1989-07-07 | 1991-01-24 | Endorecherche Inc. | Androgen derivatives for use in the inhibition of sex steroid activity |
US5364847A (en) * | 1989-03-10 | 1994-11-15 | Endorecherche | Inhibitors of sex steroid biosynthesis and methods for their production and use |
US5372996A (en) * | 1989-03-10 | 1994-12-13 | Endorecherche, Inc. | Method of treatment of androgen-related diseases |
US5494914A (en) * | 1992-05-21 | 1996-02-27 | Endorecherche | Inhibitors for testosterone 5α-reductase activity |
US5817649A (en) * | 1989-07-07 | 1998-10-06 | Endorecherche, Inc. | Combination therapy for the prophylaxis and/or treatment of benign prostatic hyperplasia |
US6423698B1 (en) | 1989-03-10 | 2002-07-23 | Endorecherche, Inc. | Combination therapy for the prophylaxis and/or treatment of benign prostatic hyperplasia |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3423507A (en) * | 1966-02-25 | 1969-01-21 | Schering Corp | Method of treating benign prostratic hypertrophy |
DE2817157A1 (en) * | 1978-04-17 | 1979-10-25 | Schering Ag | USE OF ANTIOESTROGEN AND ANTIGONADOTROP ACTING ANTIANDROGEN FOR PROPHYLAXIS AND THERAPY OF PROSTATE HYPERPLASIA |
US4235893A (en) * | 1978-05-08 | 1980-11-25 | Brodie Angela M | Ester derivatives of 4-hydroxy-4-androstene-3,17-dione and a method for inhibiting estrogen biosynthesis |
-
1983
- 1983-10-27 DE DE19833339295 patent/DE3339295A1/en active Granted
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3423507A (en) * | 1966-02-25 | 1969-01-21 | Schering Corp | Method of treating benign prostratic hypertrophy |
DE2817157A1 (en) * | 1978-04-17 | 1979-10-25 | Schering Ag | USE OF ANTIOESTROGEN AND ANTIGONADOTROP ACTING ANTIANDROGEN FOR PROPHYLAXIS AND THERAPY OF PROSTATE HYPERPLASIA |
US4235893A (en) * | 1978-05-08 | 1980-11-25 | Brodie Angela M | Ester derivatives of 4-hydroxy-4-androstene-3,17-dione and a method for inhibiting estrogen biosynthesis |
Cited By (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0181287A3 (en) * | 1984-11-06 | 1987-09-23 | Ciba-Geigy Ag | Dry substances and stable suspensions |
EP0346953A2 (en) * | 1984-11-06 | 1989-12-20 | Ciba-Geigy Ag | Micronized forms of 4-hydroxy and 4-C2-C12-acyloxy-4-androsten-3,17 diones |
EP0346953A3 (en) * | 1984-11-06 | 1990-11-22 | Ciba-Geigy Ag | Micronized forms of 4-hydroxy and 4-c2-c12-acyloxy-4-androsten-3,17 diones |
EP0181287A2 (en) * | 1984-11-06 | 1986-05-14 | Ciba-Geigy Ag | Dry substances and stable suspensions |
US5002940A (en) * | 1984-11-06 | 1991-03-26 | Ciba-Geigy Corporation | Solid drug formulations and stable suspensions |
US5585405A (en) * | 1989-03-10 | 1996-12-17 | Endorecherche Inc. | Inhibitors of sex steroid biosynthesis and methods for their production and use |
US6423698B1 (en) | 1989-03-10 | 2002-07-23 | Endorecherche, Inc. | Combination therapy for the prophylaxis and/or treatment of benign prostatic hyperplasia |
US6110906A (en) * | 1989-03-10 | 2000-08-29 | Endorecherche, Inc. | Androgen derivatives for use in the inhibition of sex steroid activity |
US5364847A (en) * | 1989-03-10 | 1994-11-15 | Endorecherche | Inhibitors of sex steroid biosynthesis and methods for their production and use |
US5372996A (en) * | 1989-03-10 | 1994-12-13 | Endorecherche, Inc. | Method of treatment of androgen-related diseases |
WO1991000733A1 (en) * | 1989-07-07 | 1991-01-24 | Endorecherche Inc. | Method of treatment of androgen-related diseases |
US5593981A (en) * | 1989-07-07 | 1997-01-14 | Endorecherche Inc. | Method and treatment of androgen-related diseases |
US5610150A (en) * | 1989-07-07 | 1997-03-11 | Endorecherche Inc. | Method of treatment of androgen-related diseases |
US5817649A (en) * | 1989-07-07 | 1998-10-06 | Endorecherche, Inc. | Combination therapy for the prophylaxis and/or treatment of benign prostatic hyperplasia |
GR900100518A (en) * | 1989-07-07 | 1991-12-10 | Endorecherche Inc | Masculine hormones derivatives |
WO1991000732A1 (en) * | 1989-07-07 | 1991-01-24 | Endorecherche Inc. | Androgen derivatives for use in the inhibition of sex steroid activity |
US5494914A (en) * | 1992-05-21 | 1996-02-27 | Endorecherche | Inhibitors for testosterone 5α-reductase activity |
Also Published As
Publication number | Publication date |
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DE3339295C2 (en) | 1992-05-27 |
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