IL23451A - 6,6-ethylenetestosterones - Google Patents

6,6-ethylenetestosterones

Info

Publication number: IL23451A
Authority: IL; Israel
Prior art keywords: acetate; ethylene; mixture; formula; ether
Prior art date: 1964-05-11

Application number

IL23451A

Other languages

English (en)

Original Assignee

Tufts College

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.)

1964-05-11

Filing date

1965-04-30

Publication date

1969-01-29

1965-04-30 Application filed by Tufts College filed Critical Tufts College

1969-01-29 Publication of IL23451A publication Critical patent/IL23451A/en

Links

-1 cyclopenten-l-yl Chemical group 0.000 claims description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 13
150000001875 compounds Chemical class 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 11
125000002252 acyl group Chemical group 0.000 claims description 5
GYMSGMABTOEEAF-UHFFFAOYSA-N 1-(cyclopenten-1-yloxy)cyclopentene Chemical compound C1CCC=C1OC1=CCCC1 GYMSGMABTOEEAF-UHFFFAOYSA-N 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
229920002554 vinyl polymer Polymers 0.000 claims description 2
239000000825 pharmaceutical preparation Substances 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
239000000203 mixture Substances 0.000 description 20
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
239000000243 solution Substances 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
229960001760 dimethyl sulfoxide Drugs 0.000 description 8
239000007787 solid Substances 0.000 description 8
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical group [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
229910000033 sodium borohydride Inorganic materials 0.000 description 5
239000012279 sodium borohydride Substances 0.000 description 5
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
DJPZSBANTAQNFN-UHFFFAOYSA-N Testosterone acetate Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(OC(=O)C)C1(C)CC2 DJPZSBANTAQNFN-UHFFFAOYSA-N 0.000 description 4
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
150000002084 enol ethers Chemical class 0.000 description 4
239000000284 extract Substances 0.000 description 4
239000012362 glacial acetic acid Substances 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
229960003604 testosterone Drugs 0.000 description 4
238000010626 work up procedure Methods 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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 3
PNUPHAWFSSBOAI-RLZRBERESA-N [(8r,9s,10r,13s,14s,17s)-10,13-dimethyl-6-methylidene-3-oxo-2,7,8,9,11,12,14,15,16,17-decahydro-1h-cyclopenta[a]phenanthren-17-yl] acetate Chemical compound C1C(=C)C2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)C)[C@@]1(C)CC2 PNUPHAWFSSBOAI-RLZRBERESA-N 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
CHNXZKVNWQUJIB-CEGNMAFCSA-N ethisterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 CHNXZKVNWQUJIB-CEGNMAFCSA-N 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
238000000034 method Methods 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
238000003756 stirring Methods 0.000 description 3
DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
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 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
150000002431 hydrogen Chemical group 0.000 description 2
239000000463 material Substances 0.000 description 2
229960001566 methyltestosterone Drugs 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
239000002904 solvent Substances 0.000 description 2
DJPZSBANTAQNFN-PXQJOHHUSA-N testosterone acetate Chemical class C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)C)[C@@]1(C)CC2 DJPZSBANTAQNFN-PXQJOHHUSA-N 0.000 description 2
150000003515 testosterones Chemical class 0.000 description 2
BPLKQGGAXWRFOE-UHFFFAOYSA-M trimethylsulfoxonium iodide Chemical compound [I-].C[S+](C)(C)=O BPLKQGGAXWRFOE-UHFFFAOYSA-M 0.000 description 2
HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 1
SZQVEGOXJYTLLB-UHFFFAOYSA-N 3-cyclopentylpropanoyl chloride Chemical compound ClC(=O)CCC1CCCC1 SZQVEGOXJYTLLB-UHFFFAOYSA-N 0.000 description 1
MFEILWXBDBCWKF-UHFFFAOYSA-N 3-phenylpropanoyl chloride Chemical compound ClC(=O)CCC1=CC=CC=C1 MFEILWXBDBCWKF-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
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 1
238000010521 absorption reaction Methods 0.000 description 1
150000001266 acyl halides Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
239000002585 base Substances 0.000 description 1
239000012267 brine Substances 0.000 description 1
HDHXNQZPJLXWJK-UHFFFAOYSA-N carbonyl dichloride;n,n-dimethylformamide Chemical compound ClC(Cl)=O.CN(C)C=O HDHXNQZPJLXWJK-UHFFFAOYSA-N 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
DKWOHBPRFZIUQL-UHFFFAOYSA-N dimethyl-methylidene-oxo-$l^{6}-sulfane Chemical compound C[S+](C)([CH2-])=O DKWOHBPRFZIUQL-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
229960000445 ethisterone Drugs 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
150000004694 iodide salts Chemical class 0.000 description 1
239000000155 melt Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000010414 supernatant solution Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000001665 trituration Methods 0.000 description 1

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
- 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
- A61K31/569—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 substituted in position 17 alpha, e.g. ethisterone
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
- 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)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Epidemiology (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

IL23451A 1964-05-11 1965-04-30 6,6-ethylenetestosterones IL23451A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US36660464A	1964-05-11	1964-05-11

Publications (1)

Publication Number	Publication Date
IL23451A true IL23451A (en)	1969-01-29

Family

ID=23443705

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL23451A IL23451A (en)	1964-05-11	1965-04-30	6,6-ethylenetestosterones

Country Status (9)

Country	Link
BE (1)	BE663708A (fr)
CH (1)	CH435263A (fr)
DE (1)	DE1493258A1 (fr)
DK (1)	DK117349B (fr)
FR (2)	FR4753M (fr)
GB (1)	GB1070329A (fr)
IL (1)	IL23451A (fr)
NL (1)	NL6505879A (fr)
SE (1)	SE310176B (fr)

1965
- 1965-04-28 GB GB17967/65A patent/GB1070329A/en not_active Expired
- 1965-04-30 IL IL23451A patent/IL23451A/en unknown
- 1965-05-07 FR FR16225A patent/FR4753M/fr not_active Expired
- 1965-05-07 FR FR16231A patent/FR1455109A/fr not_active Expired
- 1965-05-07 DE DE19651493258 patent/DE1493258A1/de active Pending
- 1965-05-10 NL NL6505879A patent/NL6505879A/xx unknown
- 1965-05-10 CH CH652965A patent/CH435263A/fr unknown
- 1965-05-10 BE BE663708D patent/BE663708A/xx unknown
- 1965-05-11 DK DK237365AA patent/DK117349B/da unknown
- 1965-05-11 SE SE6155/65A patent/SE310176B/xx unknown

Also Published As

Publication number	Publication date
FR1455109A (fr)	1966-04-01
NL6505879A (fr)	1965-11-12
CH435263A (fr)	1967-05-15
DE1493258A1 (de)	1969-11-20
DK117349B (da)	1970-04-20
SE310176B (fr)	1969-04-21
GB1070329A (en)	1967-06-01
BE663708A (fr)	1965-11-10
FR4753M (fr)	1967-01-16

Publication	Publication Date	Title
US3682983A (en)	1972-08-08	Preparation of {66 {11 {11 -17 ethinyl steroids
US3247189A (en)	1966-04-19	3, 19 and 20 oxygenated-delta5-pregnenes
US3407212A (en)	1968-10-22	Processes for cyclizing compounds having the 8a carbamyl,2- oxo-naphthalene moiety to pyrrolidones and reacting the latter with a sulfonyl halide
US3346602A (en)	1967-10-10	13beta-alkyl-11-alkylgona-1, 3, 5 (10)-trien-17-ones, ethers and esters thereof
US3637770A (en)	1972-01-25	Process for the production of 16alpha 17alpha-dihydroxy-19-nor-progesterone
US3497498A (en)	1970-02-24	6,6-ethylenetestosterones
US3773758A (en)	1973-11-20	7alpha-cyano-17-hydroxy-3-oxo-17alpha-pregn-4-ene-21-carboxylic acid ypsilon-lactone and related compounds
IL23451A (en)	1969-01-29	6,6-ethylenetestosterones
US3753979A (en)	1973-08-21	Substituted 1,2alpha-methylene-6,7alpha-halomethylene-20-spirox-4-en-3-ones or 3-ols and acyl esters thereof
US3342813A (en)	1967-09-19	Process for the preparation of butenolides derived from cyclopentano perhydro phenanthrenes
US3272803A (en)	1966-09-13	2, 2-ethylenetestosterones
US3280114A (en)	1966-10-18	17-lowerr alkyl ethers of 6-chloro-delta4, 6-pregnadien-17alpha-ol-3, 20-dione
US3083200A (en)	1963-03-26	22-halo-20-spirox-4-ene-3, 21-diones and process for preparation
US3079408A (en)	1963-02-26	Ig-bisoxygenated iy-haloestra-
US3313703A (en)	1967-04-11	19-nor-deta4, 9, 11-pregnatriene-3, 20-dione, process and intermediates
US3169958A (en)	1965-02-16	3-oxygenated-5alpha-halogen-6beta:19-oxido-pregnanes
US3280149A (en)	1966-10-18	17-oxygenated estr-5(10)-en-3-ones and intermediates
Bernstein et al.	1957	Synthesis of 17α-Methyl-4-androstene-3β, 17, β-diol
US3018285A (en)	1962-01-23	20-ethylene dioxy-pregnane-3-one derivatives
US3083198A (en)	1963-03-26	Novel 2-alkoxy steroids and processes for preparing the same
US3099659A (en)	1963-07-30	Steroidal lactones
US3155660A (en)	1964-11-03	Process for the preparation of 19-nor-delta4, 9-pregnadien-3, 20-dione and intermediaes
Moore et al.	1964	Heterocyclic Studies. X. A Steroidal 1, 2-Diazepin-4-one1
US3325536A (en)	1967-06-13	C-norpregnanes
US2934532A (en)	1960-04-26	Delta 5-11, 20-diketo-pregnene 3-ketals and process