NO134214B - - Google Patents

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Info

Publication number: NO134214B
Authority: NO; Norway
Prior art keywords: diene; oxa; estra; gona; seco
Prior art date: 1967-01-06

Application number

NO6839A

Other languages

English (en)

Norwegian (no)

Other versions

NO134214C (fr

Inventor

R Joly

J Warnant

J Jolly

Original Assignee

Roussel Uclaf

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.)

1967-01-06

Filing date

1968-01-05

Publication date

1976-05-24

1968-01-05 Application filed by Roussel Uclaf filed Critical Roussel Uclaf

1976-05-24 Publication of NO134214B publication Critical patent/NO134214B/no

1976-09-01 Publication of NO134214C publication Critical patent/NO134214C/no

Links

239000003795 chemical substances by application Substances 0.000 claims description 19
238000002360 preparation method Methods 0.000 claims description 19
238000000034 method Methods 0.000 claims description 11
230000002378 acidificating effect Effects 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
125000001589 carboacyl group Chemical group 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
239000000203 mixture Substances 0.000 description 22
150000001875 compounds Chemical class 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
238000007269 dehydrobromination reaction Methods 0.000 description 7
239000012299 nitrogen atmosphere Substances 0.000 description 7
239000002798 polar solvent Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 6
PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 6
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 5
HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 5
239000000391 magnesium silicate Substances 0.000 description 5
229910052919 magnesium silicate Inorganic materials 0.000 description 5
235000019792 magnesium silicate Nutrition 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000007858 starting material Substances 0.000 description 5
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
-1 3,5-dione steroid Chemical class 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
230000031709 bromination Effects 0.000 description 4
238000005893 bromination reaction Methods 0.000 description 4
239000000284 extract Substances 0.000 description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical group [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000010828 elution Methods 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
229910052744 lithium Inorganic materials 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
239000000047 product Substances 0.000 description 3
150000003431 steroids Chemical class 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
125000000468 ketone group Chemical group 0.000 description 2
AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
230000000962 progestomimetic effect Effects 0.000 description 2
238000000746 purification Methods 0.000 description 2
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 2
238000003756 stirring Methods 0.000 description 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
MXQNHNJSQKBNDC-UHFFFAOYSA-N 2-methoxy-2h-pyran Chemical class COC1OC=CC=C1 MXQNHNJSQKBNDC-UHFFFAOYSA-N 0.000 description 1
MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical class C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
230000001195 anabolic effect Effects 0.000 description 1
230000001548 androgenic effect Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
238000010908 decantation Methods 0.000 description 1
150000001993 dienes Chemical class 0.000 description 1
238000004821 distillation Methods 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000002576 ketones Chemical group 0.000 description 1
XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
229910052808 lithium carbonate Inorganic materials 0.000 description 1
239000000155 melt Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
150000002914 oxasteroids Chemical class 0.000 description 1
239000000583 progesterone congener Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229960001124 trientine Drugs 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J73/00—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms
- C07J73/001—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms by one hetero atom
- C07J73/003—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms by one hetero atom by oxygen as hetero atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Steroid Compounds (AREA)
Paints Or Removers (AREA)

NO6839A 1967-01-06 1968-01-05 NO134214C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR90265A FR1526962A (fr)	1967-01-06	1967-01-06	Nouveau procédé de préparation d'un composé gonatriénique et produits en résultant
FR90264A FR1526961A (fr)	1967-01-06	1967-01-06	Nouveaux 4-oxa stéroïdes et procédé de préparation

Publications (2)

Publication Number	Publication Date
NO134214B true NO134214B (fr)	1976-05-24
NO134214C NO134214C (fr)	1976-09-01

Family

ID=26174488

Family Applications (3)

Application Number	Title	Priority Date
NO6839A NO134214C (fr)	1967-01-06	1968-01-05
NO69154A NO134159C (fr)	1967-01-06	1969-01-15
NO69153A NO134213C (fr)	1967-01-06	1969-01-15

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
NO69154A NO134159C (fr)	1967-01-06	1969-01-15
NO69153A NO134213C (fr)	1967-01-06	1969-01-15

Country Status (13)

Country	Link
US (1)	US3499913A (fr)
AT (4)	AT284353B (fr)
BE (1)	BE708997A (fr)
CH (1)	CH483452A (fr)
DE (1)	DE1668641C3 (fr)
DK (3)	DK135630B (fr)
ES (2)	ES348970A1 (fr)
FR (2)	FR1526961A (fr)
GB (3)	GB1206816A (fr)
IL (3)	IL29150A (fr)
NL (1)	NL6800211A (fr)
NO (3)	NO134214C (fr)
SE (1)	SE328882B (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU201091B (en)	1985-12-26	1990-09-28	Mitsubishi Chem Ind	Process for producing gonatriene derivatives and pharmaceutical compositions comprising same
US5434274A (en) *	1991-12-20	1995-07-18	Washington University	Benz(epsilon)indene compounds
US5206415A (en) *	1991-12-20	1993-04-27	Washington University	Tricyclic steroid analogs

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3138617A (en) *	1959-08-27	1964-06-23	Roussel Uclaf	Processes for the production of 19-nor-delta4-[9beta], [10alpha]-androstenes and intermediates
FR1366725A (fr) *	1961-01-31	1964-07-17	Roussel Uclaf	Nouveaux oxa-stéroïdes, leur préparation et leur utilisation en synthèse stéroïdienne
US3085098A (en) *	1960-07-29	1963-04-09	Roussel Uclaf	Process for the preparation of 17beta-oxy-genated-delta4, 9(10)-estradiene-3-one
US3102145A (en) *	1961-06-28	1963-08-27	Roussel Uclaf	Intermediate in the preparation of 19-nor-progesterone
FR1305992A (fr) *	1961-07-21	1962-10-13	Roussel Uclaf	Procédé de préparation de certains 19-nor stéroïdes et produits utilisés dans ce procédé
BE657260A (fr) *	1962-03-06
US3422121A (en) *	1965-08-13	1969-01-14	Merck & Co Inc	Process for the preparation of 13-lower alkyl-gona-4,8(14),9-triene-3,17-dione

1967
- 1967-01-06 FR FR90264A patent/FR1526961A/fr not_active Expired
- 1967-01-06 FR FR90265A patent/FR1526962A/fr not_active Expired
- 1967-12-18 IL IL29150A patent/IL29150A/en unknown
- 1967-12-18 IL IL38246A patent/IL38246A/xx unknown
- 1967-12-18 IL IL38446A patent/IL38446A/en unknown
- 1967-12-22 CH CH1810067A patent/CH483452A/fr not_active IP Right Cessation
1968
- 1968-01-03 US US695364A patent/US3499913A/en not_active Expired - Lifetime
- 1968-01-05 DE DE1668641A patent/DE1668641C3/de not_active Expired
- 1968-01-05 NL NL6800211A patent/NL6800211A/xx unknown
- 1968-01-05 BE BE708997D patent/BE708997A/xx not_active IP Right Cessation
- 1968-01-05 AT AT1123768A patent/AT284353B/de not_active IP Right Cessation
- 1968-01-05 AT AT15168A patent/AT283610B/de not_active IP Right Cessation
- 1968-01-05 ES ES348970A patent/ES348970A1/es not_active Expired
- 1968-01-05 AT AT1123868A patent/AT281318B/de not_active IP Right Cessation
- 1968-01-05 ES ES348969A patent/ES348969A1/es not_active Expired
- 1968-01-05 NO NO6839A patent/NO134214C/no unknown
- 1968-01-05 AT AT1123668A patent/AT287933B/de not_active IP Right Cessation
- 1968-01-05 DK DK3568AA patent/DK135630B/da not_active IP Right Cessation
- 1968-01-05 SE SE00149/68A patent/SE328882B/xx unknown
- 1968-01-08 GB GB995/68A patent/GB1206816A/en not_active Expired
- 1968-01-08 GB GB6774/70A patent/GB1206818A/en not_active Expired
- 1968-01-08 GB GB6773/70A patent/GB1206817A/en not_active Expired
1969
- 1969-01-15 NO NO69154A patent/NO134159C/no unknown
- 1969-01-15 NO NO69153A patent/NO134213C/no unknown
1970
- 1970-12-14 DK DK632970AA patent/DK130307B/da not_active IP Right Cessation
- 1970-12-14 DK DK632870AA patent/DK126936B/da not_active IP Right Cessation

Also Published As

Publication number	Publication date
DE1793691A1 (de)	1972-07-27
SE328882B (fr)	1970-09-28
NO134159B (fr)	1976-05-18
IL38246A (en)	1972-10-29
GB1206818A (en)	1970-09-30
NL6800211A (fr)	1968-07-08
GB1206817A (en)	1970-09-30
GB1206816A (en)	1970-09-30
AT284353B (de)	1970-09-10
DE1668641A1 (de)	1972-03-02
CH483452A (fr)	1969-12-31
BE708997A (fr)	1968-07-05
NO134213B (fr)	1976-05-24
DK130307B (da)	1975-02-03
AT287933B (de)	1971-02-10
ES348970A1 (es)	1969-08-16
DE1668641B2 (de)	1974-08-08
DK135630C (fr)	1977-10-31
ES348969A1 (es)	1969-03-16
IL29150A (en)	1972-09-28
FR1526961A (fr)	1968-05-31
DE1668641C3 (de)	1975-03-20
DK135630B (da)	1977-05-31
NO134214C (fr)	1976-09-01
AT281318B (de)	1970-05-11
NO134159C (fr)	1976-08-25
FR1526962A (fr)	1968-05-31
IL38446A (en)	1972-12-29
AT283610B (de)	1970-08-10
DK126936B (da)	1973-09-03
DE1793691B2 (de)	1976-05-13
US3499913A (en)	1970-03-10
NO134213C (fr)	1976-09-01
DK130307C (fr)	1975-06-30

Publication	Publication Date	Title
Manson et al.	1963	Steroidal heterocycles. VII. 1 Androstano [2, 3-d] isoxazoles and related compounds
FI83424C (fi)	1991-07-10	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara substituerade androsta-1,4-dien-3,17-dioner.
Numazawa et al.	1982	Stereospecific synthesis of 16. alpha.-hydroxy-17-oxo steroids by controlled alkaline hydrolysis of corresponding 16-bromo-17-ketones and its reaction mechanism
EP0326340B1 (fr)	1993-12-08	Synthèse de dérivés de 6-méthylène-androsta-1,4-diène-3,17-diones
Andre et al.	1952	Direct Introduction of Oxygen into the Steroid Nucleus. I. Studies on the Chromic Anhydride Oxidation of Dehydroisoandrosterone Acetate Dibromide1
US3128283A (en)	1964-04-07	17-oxygenated oxa-steroids and intermediates thereto
Eppstein et al.	1954	Microbiological Transformations of Steroids. 1 X. The Oxygenation of Androgens by Rhizopus2
Johnson et al.	1956	Steroid Total Synthesis—Hydrochrysene Approach. VIII. 1 dl-3β, 11β-Dihydroxyandrostane-17-one
US3309387A (en)	1967-03-14	19-lower alkyl androstanes and pregnanes
NO134214B (fr)	1976-05-24
NO146682B (no)	1982-08-09	Tetningsmatel for isolerte roerledninger
Nussbaum et al.	1961	Enol ethers of steroidal Δ4-3-ketones
Tsuda et al.	1956	Cholesterol and related compounds. V. Synthesis of aza-D-homosteroids
US3210388A (en)	1965-10-05	13alpha-fluoro-17beta-methyl-18-nor steroids
DK171850B1 (da)	1997-07-07	Fremgangsmåde til fremstilling af 17alfa-ethynyl-17beta-hydroxy-18-methyl-4,15-østradien-3-on og mellemprodukter til anvendelse ved fremgangsmåden
US3072646A (en)	1963-01-08	Novel 6-chloro-17alpha-haloethynyl-19-norandrostadienes and processes
Julian et al.	1955	Sterols. XV. 1 Cortisone and Analogs. Part 1. 16α-Hydroxy and 16α, 17α-Epoxy Analogs of Cortisone
DK142707B (da)	1980-12-29	Analogifremgangsmåde til fremstilling af 19-oxygenerede steroidforbindelser.
NO304115B1 (no)	1998-10-26	FremgangsmÕte for fremstilling av 10<beta>-H-steroider
Engel et al.	1983	Favorskii rearrangements of. alpha.-halogenated acetylcycloalkanes. 4. Stereochemistry of cyclopropanonic rearrangements and the influence of steric factors on the competing formation of. alpha.-hydroxy ketones
Marker	1947	Steroidal Sapogenins. No. 167. Pregnene Derivatives from Nologenin
US2840574A (en)	1958-06-24	Process for producing delta7-3-hydroxy steroids
US3284505A (en)	1966-11-08	19-nor-b-nortestosterones
Vingiello et al.	1965	7-Phenyldibenz [a, h] anthracene and Benzo [e] naphtho [1, 2-b] pyrene1, 2
NO124688B (fr)	1972-05-23