FI65264C - Foerfarande foer framstaellning av nya farmakologiskt aktiva steroid-spiro-oxazoliner - Google Patents

Foerfarande foer framstaellning av nya farmakologiskt aktiva steroid-spiro-oxazoliner Download PDF

Info

Publication number: FI65264C
Authority: FI; Finland
Prior art keywords: spiro; oxo; group; general formula; compound
Prior art date: 1977-03-14

Application number

FI780772A

Other languages

English (en)

Finnish (fi)

Other versions

FI780772A7 (fi

FI65264B (fi

Inventor

Sandor Solyom

Lajos Toldy

Nee Farago Katalin Szilagyi

Inge Schaefer

Eleonora Szondy

Janos Borvendeg

Nee Szente Ilona Hermann

Original Assignee

Richter Gedeon Vegyeszet

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.)

1977-03-14

Filing date

1978-03-10

Publication date

1984-04-10

1978-03-10 Application filed by Richter Gedeon Vegyeszet filed Critical Richter Gedeon Vegyeszet

1978-09-15 Publication of FI780772A7 publication Critical patent/FI780772A7/fi

1983-12-30 Application granted granted Critical

1983-12-30 Publication of FI65264B publication Critical patent/FI65264B/fi

1984-04-10 Publication of FI65264C publication Critical patent/FI65264C/fi

Links

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238000000034 method Methods 0.000 claims description 67
239000000203 mixture Substances 0.000 claims description 32
125000004432 carbon atom Chemical group C* 0.000 claims description 31
125000004043 oxo group Chemical group O=* 0.000 claims description 23
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
125000000217 alkyl group Chemical group 0.000 claims description 20
239000001257 hydrogen Substances 0.000 claims description 20
229910052739 hydrogen Inorganic materials 0.000 claims description 20
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
-1 R2 is a derivative Chemical group 0.000 claims description 11
150000003431 steroids Chemical class 0.000 claims description 11
150000002431 hydrogen Chemical group 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
125000005646 oximino group Chemical group 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 9
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
125000000676 alkoxyimino group Chemical group 0.000 claims description 6
239000002585 base Substances 0.000 claims description 6
150000002576 ketones Chemical class 0.000 claims description 6
150000004649 carbonic acid derivatives Chemical class 0.000 claims description 5
150000002084 enol ethers Chemical class 0.000 claims description 5
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 claims description 4
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 claims description 4
150000004057 1,4-benzoquinones Chemical class 0.000 claims description 3
125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 3
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239000002184 metal Substances 0.000 claims description 2
150000003673 urethanes Chemical class 0.000 claims description 2
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239000000243 solution Substances 0.000 description 42
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239000002244 precipitate Substances 0.000 description 16
239000000725 suspension Substances 0.000 description 16
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230000007935 neutral effect Effects 0.000 description 9
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229910052794 bromium Inorganic materials 0.000 description 6
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KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
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230000002401 inhibitory effect Effects 0.000 description 5
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OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 4
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QZLYKIGBANMMBK-UGCZWRCOSA-N androstane group Chemical group [C@@H]12CCC[C@@]1(C)CC[C@H]1[C@H]2CC[C@H]2CCCC[C@]12C QZLYKIGBANMMBK-UGCZWRCOSA-N 0.000 description 1
230000001864 anti-aldosterone effect Effects 0.000 description 1
230000002054 antogonadotrophic effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
238000003556 assay Methods 0.000 description 1
238000009835 boiling Methods 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
VTHIKKVKIVQWHV-UHFFFAOYSA-N chromium(6+) oxygen(2-) pyridine Chemical compound [O-2].[O-2].[O-2].[Cr+6].C1=CC=NC=C1 VTHIKKVKIVQWHV-UHFFFAOYSA-N 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 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
150000001993 dienes Chemical class 0.000 description 1
FFYPMLJYZAEMQB-UHFFFAOYSA-N diethyl pyrocarbonate Chemical compound CCOC(=O)OC(=O)OCC FFYPMLJYZAEMQB-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
GZRYBYIBLHMWCD-UHFFFAOYSA-N dimethyl(methylidene)-$l^{4}-sulfane Chemical compound CS(C)=C GZRYBYIBLHMWCD-UHFFFAOYSA-N 0.000 description 1
DKWOHBPRFZIUQL-UHFFFAOYSA-N dimethyl-methylidene-oxo-$l^{6}-sulfane Chemical compound C[S+](C)([CH2-])=O DKWOHBPRFZIUQL-UHFFFAOYSA-N 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
239000003792 electrolyte Substances 0.000 description 1
150000002081 enamines Chemical class 0.000 description 1
230000002124 endocrine Effects 0.000 description 1
230000001076 estrogenic effect Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000005048 flame photometry Methods 0.000 description 1
230000003054 hormonal effect Effects 0.000 description 1
231100000508 hormonal effect Toxicity 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
XIQUJVRFXPBMHS-UHFFFAOYSA-N hydron;o-prop-2-enylhydroxylamine;chloride Chemical compound Cl.NOCC=C XIQUJVRFXPBMHS-UHFFFAOYSA-N 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
SURZCVYFPAXNGN-UHFFFAOYSA-N methyl-carbamic acid ethyl ester Chemical compound CCOC(=O)NC SURZCVYFPAXNGN-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000002395 mineralocorticoid Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
ROZPNEGZBIUWBX-UHFFFAOYSA-N n-[bis(diethylamino)phosphoryl]-n-ethylethanamine Chemical compound CCN(CC)P(=O)(N(CC)CC)N(CC)CC ROZPNEGZBIUWBX-UHFFFAOYSA-N 0.000 description 1
150000002829 nitrogen Chemical group 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
239000012071 phase Substances 0.000 description 1
229940093429 polyethylene glycol 6000 Drugs 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229930000044 secondary metabolite Natural products 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
PXLIDIMHPNPGMH-UHFFFAOYSA-N sodium chromate Chemical compound [Na+].[Na+].[O-][Cr]([O-])(=O)=O PXLIDIMHPNPGMH-UHFFFAOYSA-N 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
238000009495 sugar coating Methods 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229960001712 testosterone propionate Drugs 0.000 description 1
238000001665 trituration Methods 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
230000002485 urinary effect Effects 0.000 description 1
230000004584 weight gain Effects 0.000 description 1
235000019786 weight gain Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/006—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton spiro-condensed
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/38—Drugs for disorders of the endocrine system of the suprarenal hormones
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0088—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 containing unsubstituted amino radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J51/00—Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
- 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
- C07J53/002—Carbocyclic rings fused
- C07J53/004—3 membered carbocyclic rings

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Diabetes (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
Hematology (AREA)
Endocrinology (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

FI780772A 1977-03-14 1978-03-10 Foerfarande foer framstaellning av nya farmakologiskt aktiva steroid-spiro-oxazoliner FI65264C (fi)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HUGO001364		1977-03-14
HU77GO1364A HU179711B (en)	1977-03-14	1977-03-14	Process for preparing steroid-spiro-oxazolidinone derivatives

Publications (3)

Publication Number	Publication Date
FI780772A7 FI780772A7 (fi)	1978-09-15
FI65264B FI65264B (fi)	1983-12-30
FI65264C true FI65264C (fi)	1984-04-10

Family

ID=10996830

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI780772A FI65264C (fi)	1977-03-14	1978-03-10	Foerfarande foer framstaellning av nya farmakologiskt aktiva steroid-spiro-oxazoliner

Country Status (19)

Country	Link
US (1)	US4180505A (de)
JP (1)	JPS6050199B2 (de)
AT (1)	AT370113B (de)
AU (1)	AU522931B2 (de)
BE (1)	BE864689A (de)
CA (1)	CA1115691A (de)
CH (1)	CH639399A5 (de)
DE (1)	DE2811101A1 (de)
DK (1)	DK111578A (de)
ES (1)	ES467861A1 (de)
FI (1)	FI65264C (de)
FR (1)	FR2383970A1 (de)
GB (1)	GB1599464A (de)
HU (1)	HU179711B (de)
IL (1)	IL54169A (de)
NL (1)	NL7802784A (de)
NO (1)	NO780867L (de)
SE (1)	SE7802666L (de)
SU (2)	SU931109A3 (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU178397B (en) *	1978-04-01	1982-04-28	Gyogyszerkutato Intezet	Process for preparing substituted derivatives of steroid-spiro-oxazolidione derivatives
HU179980B (en) *	1979-12-28	1983-01-28	Gyogyszerkutato Intezet	Process for preparing substituted steroid-spiro-oxazolidinone derivatives
HU181066B (en) *	1980-03-12	1983-05-30	Gyogyszerkutato Intezet	Process for preparing steroid -spiro-oxathiazolidine derivatives
US4460509A (en) *	1981-08-19	1984-07-17	Beth Israel Medical Center	Chemical synthesis
US7214825B2 (en)	2003-10-17	2007-05-08	Honeywell International Inc.	O-(3-chloropropenyl) hydroxylamine free base

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3272801A (en) *	1964-11-19	1966-09-13	American Home Prod	Steroidal spiro-oxazolidinones
NL7107998A (de) *	1970-07-09	1972-01-11
HU167833B (de) *	1973-07-09	1975-12-25
US4018774A (en) *	1976-02-13	1977-04-19	E. R. Squibb & Sons, Inc.	Steroidal [16α,17-d]isoxazolidines

1977
- 1977-03-14 HU HU77GO1364A patent/HU179711B/hu unknown
1978
- 1978-03-01 IL IL54169A patent/IL54169A/xx unknown
- 1978-03-03 AU AU33834/78A patent/AU522931B2/en not_active Expired
- 1978-03-08 SE SE7802666A patent/SE7802666L/xx unknown
- 1978-03-09 BE BE1008755A patent/BE864689A/xx not_active IP Right Cessation
- 1978-03-10 AT AT0175378A patent/AT370113B/de not_active IP Right Cessation
- 1978-03-10 FI FI780772A patent/FI65264C/fi not_active IP Right Cessation
- 1978-03-13 DK DK111578A patent/DK111578A/da not_active Application Discontinuation
- 1978-03-13 GB GB9862/78A patent/GB1599464A/en not_active Expired
- 1978-03-13 CA CA298,768A patent/CA1115691A/en not_active Expired
- 1978-03-13 SU SU782590453A patent/SU931109A3/ru active
- 1978-03-13 CH CH269078A patent/CH639399A5/de not_active IP Right Cessation
- 1978-03-13 NO NO780867A patent/NO780867L/no unknown
- 1978-03-13 FR FR7807109A patent/FR2383970A1/fr active Granted
- 1978-03-14 ES ES467861A patent/ES467861A1/es not_active Expired
- 1978-03-14 NL NL7802784A patent/NL7802784A/xx not_active Application Discontinuation
- 1978-03-14 JP JP53029212A patent/JPS6050199B2/ja not_active Expired
- 1978-03-14 US US05/886,349 patent/US4180505A/en not_active Expired - Lifetime
- 1978-03-14 DE DE19782811101 patent/DE2811101A1/de not_active Withdrawn
1979
- 1979-11-26 SU SU792846547A patent/SU915806A3/ru active

Also Published As

Publication number	Publication date
HU179711B (en)	1982-11-29
AU522931B2 (en)	1982-07-01
SU931109A3 (ru)	1982-05-23
IL54169A (en)	1981-12-31
CH639399A5 (de)	1983-11-15
FR2383970A1 (fr)	1978-10-13
IL54169A0 (en)	1978-06-15
ES467861A1 (es)	1978-10-16
US4180505A (en)	1979-12-25
AU3383478A (en)	1979-09-06
NL7802784A (nl)	1978-09-18
JPS53116372A (en)	1978-10-11
GB1599464A (en)	1981-10-07
BE864689A (fr)	1978-09-11
NO780867L (no)	1978-09-15
AT370113B (de)	1983-03-10
FR2383970B1 (de)	1981-12-04
SE7802666L (sv)	1978-09-15
DK111578A (da)	1978-09-15
FI780772A7 (fi)	1978-09-15
JPS6050199B2 (ja)	1985-11-07
FI65264B (fi)	1983-12-30
ATA175378A (de)	1982-07-15
SU915806A3 (en)	1982-03-23
CA1115691A (en)	1982-01-05
DE2811101A1 (de)	1978-10-19

Legal Events

Date	Code	Title	Description
2004-08-31	MM	Patent lapsed	Owner name: RICHTER GEDEON VEGYESZETI GYAR RT

Publication	Publication Date	Title
FI77669B (fi)	1988-12-30	20-spiroxaner och analoger, som innehaoller en oeppen ring e, foerfarande foer deras framstaellning samt dessa innehaollande farmaceutiska preparat.
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
FI95710B (fi)	1995-11-30	9-alfa-hydroksi-steroidit, menetelmä niiden valmistamiseksi ja menetelmä vastaavien 9(11)-dehydro-johdannaisten valmistamiseksi
SU1715205A3 (ru)	1992-02-23	Способ получени стероидов, замещенных спирановым циклом
FI95711C (fi)	1996-03-11	Menetelmä terapeuttisesti käyttökelpoisten 4-substituoitujen 17 -(syklopropyylioksi)androst-5-eenijohdannaisten valmistamiseksi, jotka ovat hyödyllisiä C17-20-lyaasi-inhibiittoreina
HU210532A9 (en)	1995-04-28	19,11beta-bridged steroides, process for producing them and pharmaceutical compositions containing them
IE60321B1 (en)	1994-06-29	"11alpha -alkynyl-estrenes and -estradienes, their production and pharmaceutical preparations containing them"
NO178768B (no)	1996-02-19	11 disse
DK157892B (da)	1990-02-26	Fremgangsmaade til fremstilling af 3beta,7beta-dihydroxy-delta5-steroider
Campbell et al.	1958	6-Methyl Steroids in the Androstane Series1
FI65264C (fi)	1984-04-10	Foerfarande foer framstaellning av nya farmakologiskt aktiva steroid-spiro-oxazoliner
US5232915A (en)	1993-08-03	9α-hydroxy-19,11β-bridged steroids, their production and pharmaceutical preparations containing these steroids
FI83225C (fi)	1991-06-10	Foerfarande foer framstaellning av terapeutiskt verkande 9 ,11 -epoxisteroider.
WO2009059765A2 (en)	2009-05-14	Process for the preparation of drospirenone
DK167766B1 (da)	1993-12-13	17beta-(cyclopropyloxy(thio))-androst-5-en-3beta-ol- og -4-en-3-on-forbindelser og fremgangsmaade til deres fremstilling
JPS62158300A (ja)	1987-07-14	１０β−アルキニルエストレン誘導体およびそれらの製造法
FI58779C (fi)	1981-04-10	Foerfarande foer framstaellning av terapeutiskt anvaendbara aldosteron-antagonistiska steroidfoereningar av spiroxanserien med en syrehaltig grupp i 19-staellningen
DE4042007A1 (de)	1992-06-25	6,7-modifizierte-11(beta)-aryl-4-estrene
NZ256865A (en)	1996-04-26	19,11-bridged 4-estrene derivatives and pharmaceutical compositions
FI84273C (fi)	1991-11-11	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 6-substituerad androsta-1,4-dien-3,17 dionderivat.
US3455909A (en)	1969-07-15	3-desoxy steroidal-1,4-diene lactones and spiroethers
HU182759B (en)	1984-03-28	Process for preparing 5beta-hydroxy-delta up 6-steroid derivatives
US3491089A (en)	1970-01-20	11-oxygenated steroids and process for their preparation
FI84487B (fi)	1991-08-30	1-alkyl-androsta-1,4-dien-3, 17-dioner som anvaends foer kontraseption och en komposition innehaollande desamma.
HU181066B (en)	1983-05-30	Process for preparing steroid -spiro-oxathiazolidine derivatives