CH416609A - Verfahren zur Herstellung neuer 17-Cycloalkenyläther von 17B-Hydroxysteroiden der Androstanreihe - Google Patents

Verfahren zur Herstellung neuer 17-Cycloalkenyläther von 17B-Hydroxysteroiden der Androstanreihe

Info

Publication number: CH416609A
Authority: CH; Switzerland
Prior art keywords: sep; ether; cyclopentenyl; new; ethers
Prior art date: 1961-04-12

Application number

CH444162A

Other languages

German (de)

English (en)

Inventor

Alberto Prof Ercoli

Rinaldo Dr Gardi

Original Assignee

Vismara Francesco Spa

Priority date (The priority date 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 date listed.)

1961-04-12

Filing date

1962-04-11

Publication date

1966-07-15

1962-04-11 Application filed by Vismara Francesco Spa filed Critical Vismara Francesco Spa

1966-07-15 Publication of CH416609A publication Critical patent/CH416609A/de

Links

238000000034 method Methods 0.000 title claims description 7
150000001441 androstanes Chemical class 0.000 title description 2
238000002360 preparation method Methods 0.000 title description 2
BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims description 16
150000001875 compounds Chemical class 0.000 claims description 10
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
125000002252 acyl group Chemical group 0.000 claims description 2
125000001033 ether group Chemical group 0.000 claims description 2
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
-1 hydroxy steroids Chemical class 0.000 claims description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
150000003254 radicals Chemical class 0.000 claims description 2
KVUXYQHEESDGIJ-UHFFFAOYSA-N 10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthrene-3,16-diol Chemical compound C1CC2CC(O)CCC2(C)C2C1C1CC(O)CC1(C)CC2 KVUXYQHEESDGIJ-UHFFFAOYSA-N 0.000 claims 1
150000002170 ethers Chemical class 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 17
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
239000000203 mixture Substances 0.000 description 16
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 12
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 9
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
QJKUIUCQENFWSS-UHFFFAOYSA-N 1,1-diethoxycyclopentane Chemical compound CCOC1(OCC)CCCC1 QJKUIUCQENFWSS-UHFFFAOYSA-N 0.000 description 5
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 5
229960003604 testosterone Drugs 0.000 description 5
229960001566 methyltestosterone Drugs 0.000 description 4
GCKMFJBGXUYNAG-UHFFFAOYSA-N 17alpha-methyltestosterone Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(C)(O)C1(C)CC2 GCKMFJBGXUYNAG-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000001548 androgenic effect Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
230000003054 hormonal effect Effects 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
229960004719 nandrolone Drugs 0.000 description 3
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 description 3
OEOFQABUOAWYMP-UHFFFAOYSA-N oxiren-2-ol Chemical compound OC1=CO1 OEOFQABUOAWYMP-UHFFFAOYSA-N 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
239000002904 solvent Substances 0.000 description 3
FEOWWOCANLUVIT-SSCHMFMQSA-N (8r,9s,10s,13s,14s,17s)-10,13-dimethyl-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-ol Chemical compound C1C=CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC21 FEOWWOCANLUVIT-SSCHMFMQSA-N 0.000 description 2
GYMSGMABTOEEAF-UHFFFAOYSA-N 1-(cyclopenten-1-yloxy)cyclopentene Chemical class C1CCC=C1OC1=CCCC1 GYMSGMABTOEEAF-UHFFFAOYSA-N 0.000 description 2
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 2
150000001241 acetals Chemical class 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
230000001195 anabolic effect Effects 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
239000003054 catalyst Substances 0.000 description 2
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 2
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
BGMIRDHBNWQSGE-UHFFFAOYSA-N hypochlorous acid;pyridine Chemical compound ClO.C1=CC=NC=C1 BGMIRDHBNWQSGE-UHFFFAOYSA-N 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
DKCLFTBKKHWBQS-YNZDMMAESA-N (5s,8r,9s,10s,13s,14s,17s)-17-hydroxy-2-(hydroxymethylidene)-10,13-dimethyl-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-one Chemical compound C1C(=O)C(=CO)C[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@H]21 DKCLFTBKKHWBQS-YNZDMMAESA-N 0.000 description 1
MWUDABUKTZAZCX-UHFFFAOYSA-N 1,1-diethoxycyclohexane Chemical compound CCOC1(OCC)CCCCC1 MWUDABUKTZAZCX-UHFFFAOYSA-N 0.000 description 1
AGWFDZMDKNQQHG-UHFFFAOYSA-N 1,1-dimethoxycyclopentane Chemical compound COC1(OC)CCCC1 AGWFDZMDKNQQHG-UHFFFAOYSA-N 0.000 description 1
YYWMPTGXJBPRND-YNZDMMAESA-N 17beta-Hydroxy-androstano[3,2-c]isoxazole Chemical compound C[C@]12CC[C@H]3[C@@H](CC[C@H]4Cc5nocc5C[C@]34C)[C@@H]1CC[C@@H]2O YYWMPTGXJBPRND-YNZDMMAESA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
HHBZZTKMMLDNDN-UHFFFAOYSA-N 2-butan-2-yloxybutane Chemical compound CCC(C)OC(C)CC HHBZZTKMMLDNDN-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
BOTLEXFFFSMRLQ-UHFFFAOYSA-N cyclopentyloxycyclopentane Chemical compound C1CCCC1OC1CCCC1 BOTLEXFFFSMRLQ-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000006266 etherification reaction Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
231100000508 hormonal effect Toxicity 0.000 description 1
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
150000002545 isoxazoles Chemical class 0.000 description 1
239000000155 melt Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- 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
- A61K31/568—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 substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
- 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
- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Steroid Compounds (AREA)

CH444162A 1961-04-12 1962-04-11 Verfahren zur Herstellung neuer 17-Cycloalkenyläther von 17B-Hydroxysteroiden der Androstanreihe CH416609A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT679761		1961-04-12

Publications (1)

Publication Number	Publication Date
CH416609A true CH416609A (de)	1966-07-15

Family

ID=11121976

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH444162A CH416609A (de)	1961-04-12	1962-04-11	Verfahren zur Herstellung neuer 17-Cycloalkenyläther von 17B-Hydroxysteroiden der Androstanreihe

Country Status (3)

Country	Link
CH (1)	CH416609A (fr)
DK (1)	DK109328C (fr)
FR (1)	FR3612M (fr)

1962
- 1962-04-10 FR FR894033A patent/FR3612M/fr active Active
- 1962-04-11 CH CH444162A patent/CH416609A/de unknown
- 1962-04-11 DK DK166162AA patent/DK109328C/da active

Also Published As

Publication number	Publication date
DK109328C (da)	1968-04-16
FR3612M (fr)	1965-10-18

Publication	Publication Date	Title
DE2361120C2 (de)	1984-01-19	11,11-Alkylidensteroide der Östran- und Norpregnan-Reihe, Verfahren zu ihrer Herstellung und deren Verwendung
CH517725A (de)	1972-01-15	Verfahren zur Herstellung von 7a-Methylsteroiden
DE1468410A1 (de)	1969-11-20	Verfahren zur Herstellung von 16-Methylensteroiden
CH416609A (de)	1966-07-15	Verfahren zur Herstellung neuer 17-Cycloalkenyläther von 17B-Hydroxysteroiden der Androstanreihe
DE1618871C3 (de)	1974-02-21	Verfahren zur Herstellung eines Steroidketonderivates. Ausscheidung aus: 1468988
DE1518666A1 (de)	1969-06-12	Verfahren zur Herstellung von 13,14-Seco-steroiden
AT274258B (de)	1969-09-10	Verfahren zur Herstellung von neuen 7α-Methyl-Δ<4,9,11>-19-nor-androstatrienen
DE875655C (de)	1953-05-04	Verfahren zur Darstellung von Testosteron
DE1568688C3 (de)	1976-07-08	Verfahren zur Herstellung von 3-Oxo-4,6-dehydro-19-nor-steroiden, sowie 17 beta-Hydroxy-8 alpha, 10 alpha-östra-4,6-dien-3-on
DE1079040B (de)	1960-04-07	Verfahren zur Herstellung stark androgen und anabol wirksamer ?-ungesaettigter 3, 17-Diole der Androstan-bzw. 19-Norandrostanreihe
AT275059B (de)	1969-10-10	Vefahren zur Herstellung von neuen 17α-Cyanäthinylsteroiden
AT257849B (de)	1967-10-25	Verfahren zur Herstellung von neuen 20-Oxo-21-hydroxy-16, 21-methano-Δ<21>-steroiden
DE1181213B (de)	1964-11-12	Verfahren zur Herstellung neuer 17-(1'-Cycloalkenyl)-aether von 17ª‰-Hydroxy-steroiden der Androstanreihe
DE1813728C3 (de)	1976-12-16	3-Oxo-A-nor-B-homo-östr-5(10)-ene und ein Verfahren zu deren Herstellung
DE1543842C3 (de)	1974-11-07	3-Oxo-2-oxa-4,9,l 1-gonatriene, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE1159941B (de)	1963-12-27	Verfahren zur Herstellung von neuen anabol wirksamen 17-Oximino-3-keto-steroiden derAndrostanreihe
DE1668665B1 (de)	1972-05-04	Verfahren zur Herstellung von 13-Alkyl-gona-1,3,5(10)-trienen
DE2234544A1 (de)	1973-02-01	Neue 3-oxo-a-nor-b-homo-oestra-5(10),6diene und ein verfahren zur herstellung derselben
DE1468638A1 (de)	1969-10-09	Neue Cyclopentanophenanthren-Derivate und Verfahren zu deren Herstellung
DE1176131B (de)	1964-08-20	Verfahren zur Herstellung von 16-Cyan- und 16-Cyan-16, 17-seco-steroiden
DE1134371B (de)	1962-08-09	Verfahren zur Herstellung von 4ª‡-Methyl-3-oxo-5ª‡-steroiden
DE1186055B (de)	1965-01-28	Verfahren zur Herstellung von 19-Norsteroiden der Androstan- oder Pregnanreihe
CH433278A (de)	1967-04-15	Verfahren zur Herstellung eines steroiden cyclischen Acetals
CH513838A (de)	1971-10-15	Verfahren zur Herstellung von 17a-Propadiensteroiden
CH493508A (de)	1970-07-15	Verfahren zur Herstellung von mindestens eine ungesättigte Bindung im Steroidgerüst aufweisenden 17a-Acyl-16a-hydroxy-steroiden der Pregnanreihe