NO791059L - Fremgangsmaate ved fremstilling av substituerte steroid-spiro-oxazolidinonderivater - Google Patents

Fremgangsmaate ved fremstilling av substituerte steroid-spiro-oxazolidinonderivater

Info

Publication number: NO791059L
Authority: NO; Norway
Prior art keywords: denotes; group; hydrogen atom; spiro; denote
Prior art date: 1978-04-01

Application number

NO791059A

Other languages

English (en)

Norwegian (no)

Inventor

Sandor Solyom

Lajos Toldy

Katalin Szilagyi

Inge Schaefer

Eleonora Szondy

Janos Borvendeg

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.)

1978-04-01

Filing date

1979-03-30

Publication date

1979-10-02

1979-03-30 Application filed by Richter Gedeon Vegyeszet filed Critical Richter Gedeon Vegyeszet

1979-10-02 Publication of NO791059L publication Critical patent/NO791059L/no

Links

238000000034 method Methods 0.000 title claims description 17
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
150000001875 compounds Chemical class 0.000 claims description 25
239000000203 mixture Substances 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
125000002252 acyl group Chemical group 0.000 claims description 3
125000003710 aryl alkyl group Chemical group 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
239000003054 catalyst Substances 0.000 claims description 3
239000002904 solvent Substances 0.000 claims description 2
150000003431 steroids Chemical class 0.000 claims description 2
150000003573 thiols Chemical class 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
GOPUCFKUFOFEIC-UHFFFAOYSA-N 2-methyl-1,3-oxazolidine Chemical compound CC1NCCO1 GOPUCFKUFOFEIC-UHFFFAOYSA-N 0.000 claims 1
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 7
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
230000001548 androgenic effect Effects 0.000 description 6
230000000694 effects Effects 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
-1 alkyl mercaptan Chemical compound 0.000 description 4
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 4
229940088597 hormone Drugs 0.000 description 4
239000005556 hormone Substances 0.000 description 4
LXMSZDCAJNLERA-ZHYRCANASA-N spironolactone Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)SC(=O)C)C[C@@]21CCC(=O)O1 LXMSZDCAJNLERA-ZHYRCANASA-N 0.000 description 4
229960002256 spironolactone Drugs 0.000 description 4
238000007920 subcutaneous administration Methods 0.000 description 4
PQSUYGKTWSAVDQ-ZVIOFETBSA-N Aldosterone Chemical compound C([C@@]1([C@@H](C(=O)CO)CC[C@H]1[C@@H]1CC2)C=O)[C@H](O)[C@@H]1[C@]1(C)C2=CC(=O)CC1 PQSUYGKTWSAVDQ-ZVIOFETBSA-N 0.000 description 3
PQSUYGKTWSAVDQ-UHFFFAOYSA-N Aldosterone Natural products C1CC2C3CCC(C(=O)CO)C3(C=O)CC(O)C2C2(C)C1=CC(=O)CC2 PQSUYGKTWSAVDQ-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
VPGRYOFKCNULNK-ACXQXYJUSA-N Deoxycorticosterone acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)COC(=O)C)[C@@]1(C)CC2 VPGRYOFKCNULNK-ACXQXYJUSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
229960002478 aldosterone Drugs 0.000 description 3
230000001833 anti-estrogenic effect Effects 0.000 description 3
229960004486 desoxycorticosterone acetate Drugs 0.000 description 3
239000007858 starting material Substances 0.000 description 3
230000001836 utereotrophic effect Effects 0.000 description 3
238000005303 weighing Methods 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
206010030113 Oedema Diseases 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
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 2
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 2
210000004100 adrenal gland Anatomy 0.000 description 2
230000002280 anti-androgenic effect Effects 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
230000002124 endocrine Effects 0.000 description 2
230000029142 excretion Effects 0.000 description 2
210000004907 gland Anatomy 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
210000003734 kidney Anatomy 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
230000001575 pathological effect Effects 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
229960001712 testosterone propionate Drugs 0.000 description 2
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
UYIFTLBWAOGQBI-BZDYCCQFSA-N Benzhormovarine Chemical compound C([C@@H]1[C@@H](C2=CC=3)CC[C@]4([C@H]1CC[C@@H]4O)C)CC2=CC=3OC(=O)C1=CC=CC=C1 UYIFTLBWAOGQBI-BZDYCCQFSA-N 0.000 description 1
206010020571 Hyperaldosteronism Diseases 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
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
NEAPKZHDYMQZCB-UHFFFAOYSA-N N-[2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]ethyl]-2-oxo-3H-1,3-benzoxazole-6-carboxamide Chemical compound C1CN(CCN1CCNC(=O)C2=CC3=C(C=C2)NC(=O)O3)C4=CN=C(N=C4)NC5CC6=CC=CC=C6C5 NEAPKZHDYMQZCB-UHFFFAOYSA-N 0.000 description 1
206010041277 Sodium retention Diseases 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
230000003187 abdominal effect Effects 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
210000004404 adrenal cortex Anatomy 0.000 description 1
239000002170 aldosterone antagonist Substances 0.000 description 1
229940046836 anti-estrogen Drugs 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
239000002934 diuretic Substances 0.000 description 1
230000001882 diuretic effect Effects 0.000 description 1
229940030606 diuretics Drugs 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
229950002007 estradiol benzoate Drugs 0.000 description 1
239000000328 estrogen antagonist Substances 0.000 description 1
239000007888 film coating Substances 0.000 description 1
238000009501 film coating Methods 0.000 description 1
238000005048 flame photometry Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
210000002149 gonad Anatomy 0.000 description 1
230000009931 harmful effect Effects 0.000 description 1
210000002216 heart Anatomy 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000002395 mineralocorticoid Substances 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
201000009395 primary hyperaldosteronism Diseases 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
KOODSCBKXPPKHE-UHFFFAOYSA-N propanethioic s-acid Chemical compound CCC(S)=O KOODSCBKXPPKHE-UHFFFAOYSA-N 0.000 description 1
210000002307 prostate Anatomy 0.000 description 1
239000012264 purified product Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910001415 sodium ion Inorganic materials 0.000 description 1
239000011343 solid material Substances 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000009495 sugar coating Methods 0.000 description 1
230000001502 supplementing effect Effects 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229960003604 testosterone Drugs 0.000 description 1
238000001665 trituration Methods 0.000 description 1
210000002700 urine Anatomy 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000001993 wax Substances 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Diabetes (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Endocrinology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NO791059A 1978-04-01 1979-03-30 Fremgangsmaate ved fremstilling av substituerte steroid-spiro-oxazolidinonderivater NO791059L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU78GO1397A HU178397B (en)	1978-04-01	1978-04-01	Process for preparing substituted derivatives of steroid-spiro-oxazolidione derivatives

Publications (1)

Publication Number	Publication Date
NO791059L true NO791059L (no)	1979-10-02

Family

ID=10996851

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO791059A NO791059L (no)	1978-04-01	1979-03-30	Fremgangsmaate ved fremstilling av substituerte steroid-spiro-oxazolidinonderivater

Country Status (21)

Country	Link
US (1)	US4218446A (de)
JP (1)	JPS54132565A (de)
AT (1)	AT366392B (de)
AU (1)	AU523226B2 (de)
BE (1)	BE875091A (de)
CA (1)	CA1118767A (de)
CH (1)	CH640247A5 (de)
DE (1)	DE2912835A1 (de)
DK (1)	DK131379A (de)
ES (1)	ES479170A1 (de)
FI (1)	FI65785C (de)
FR (1)	FR2421181A1 (de)
GB (1)	GB2017708B (de)
HU (1)	HU178397B (de)
IL (1)	IL56913A (de)
IT (1)	IT1113203B (de)
NL (1)	NL7902528A (de)
NO (1)	NO791059L (de)
SE (1)	SE7902788L (de)
SU (1)	SU852176A3 (de)
YU (1)	YU73579A (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
FR2493324B1 (de) *	1980-11-05	1983-01-21	Roussel Uclaf
EP0116974B1 (de) *	1983-02-18	1986-10-29	Schering Aktiengesellschaft	11-Beta-Aryl-Estradiene, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Präparate
JP4606408B2 (ja) *	2003-01-21	2011-01-05	メルク・シャープ・エンド・ドーム・コーポレイション	選択的グルココルチコイド受容体調節物質としての１７−カルバモイルオキシコルチゾル誘導体
WO2007025780A2 (en) *	2005-09-02	2007-03-08	Recordati Ireland Limited	Aldosterone receptor antagonists
WO2022261774A1 (en) *	2021-06-16	2022-12-22	UNIVERSITé LAVAL	Novel inhibitors of 17b-hsd7 and uses thereof

Family Cites Families (3)

* 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
DE2253170C2 (de) *	1972-10-30	1988-12-22	Hoechst Ag, 6230 Frankfurt	Verfahren und Vorrichtung zum Behandeln einer frei schwebend geführten Materialbahn
HU179711B (en) *	1977-03-14	1982-11-29	Gyogyszerkutato Intezet	Process for preparing steroid-spiro-oxazolidinone derivatives

1978
- 1978-04-01 HU HU78GO1397A patent/HU178397B/hu unknown
1979
- 1979-03-20 IL IL56913A patent/IL56913A/xx unknown
- 1979-03-21 AT AT0213579A patent/AT366392B/de not_active IP Right Cessation
- 1979-03-26 BE BE1/9330A patent/BE875091A/xx not_active IP Right Cessation
- 1979-03-28 FR FR7907741A patent/FR2421181A1/fr active Granted
- 1979-03-28 YU YU00735/79A patent/YU73579A/xx unknown
- 1979-03-28 SE SE7902788A patent/SE7902788L/xx not_active Application Discontinuation
- 1979-03-29 US US06/025,080 patent/US4218446A/en not_active Expired - Lifetime
- 1979-03-29 FI FI791051A patent/FI65785C/fi not_active IP Right Cessation
- 1979-03-29 SU SU792744750A patent/SU852176A3/ru active
- 1979-03-30 GB GB7911132A patent/GB2017708B/en not_active Expired
- 1979-03-30 CH CH296379A patent/CH640247A5/de not_active IP Right Cessation
- 1979-03-30 CA CA000324686A patent/CA1118767A/en not_active Expired
- 1979-03-30 IT IT21432/79A patent/IT1113203B/it active
- 1979-03-30 DK DK131379A patent/DK131379A/da not_active Application Discontinuation
- 1979-03-30 AU AU45648/79A patent/AU523226B2/en not_active Ceased
- 1979-03-30 JP JP3829879A patent/JPS54132565A/ja active Pending
- 1979-03-30 DE DE19792912835 patent/DE2912835A1/de not_active Withdrawn
- 1979-03-30 NO NO791059A patent/NO791059L/no unknown
- 1979-03-30 NL NL7902528A patent/NL7902528A/xx not_active Application Discontinuation
- 1979-03-31 ES ES479170A patent/ES479170A1/es not_active Expired

Also Published As

Publication number	Publication date
ES479170A1 (es)	1979-07-01
AU523226B2 (en)	1982-07-15
FR2421181B1 (de)	1982-10-22
CA1118767A (en)	1982-02-23
GB2017708B (en)	1982-10-27
ATA213579A (de)	1981-08-15
CH640247A5 (de)	1983-12-30
SE7902788L (sv)	1979-10-02
AU4564879A (en)	1979-10-25
AT366392B (de)	1982-04-13
HU178397B (en)	1982-04-28
BE875091A (fr)	1979-09-26
IT1113203B (it)	1986-01-20
FI65785B (fi)	1984-03-30
SU852176A3 (ru)	1981-07-30
DK131379A (da)	1979-10-02
FR2421181A1 (fr)	1979-10-26
GB2017708A (en)	1979-10-10
NL7902528A (nl)	1979-10-03
US4218446A (en)	1980-08-19
IL56913A0 (en)	1979-05-31
YU73579A (en)	1982-10-31
FI65785C (fi)	1984-07-10
IL56913A (en)	1982-08-31
IT7921432A0 (it)	1979-03-30
DE2912835A1 (de)	1979-10-11
FI791051A7 (fi)	1979-10-02
JPS54132565A (en)	1979-10-15

Publication	Publication Date	Title
CELLA et al.	1959	Steroidal aldosterone blockers. II1
US20100120736A1 (en)	2010-05-13	Mineralocorticoid Receptor Antagonists
US4248791A (en)	1981-02-03	25-Hydroxy-26,26,26,27,27,27-hexafluorocholecalciferol
IE58286B1 (en)	1993-08-25	1,24-dihydroxy- 22-vitamin d3 and process for preparing same
GB1599863A (en)	1981-10-07	Pharmaceutical compositions for use in the inhibition of the biosynthesis of mevalonic acid
NO791059L (no)	1979-10-02	Fremgangsmaate ved fremstilling av substituerte steroid-spiro-oxazolidinonderivater
US4502989A (en)	1985-03-05	Aldosterone-antagonistic steroids
NO140978B (no)	1979-09-10	Analogifremgangsmaate for fremstilling av terapeutisk aktive isokinolinderivater
US3200114A (en)	1965-08-10	17-tetrahydropyranyl ethers of (3, 2-c)-pyrazole and (2, 3-d)-isoxazole derivatives o the androstane and 19-norandrostane series
EP0245276A1 (de)	1987-11-19	1$g(a).7$g(a)-DITHIOSUBSTITUIERTE SPIROLACTONE, VERFAHREN ZU IHRER HERSTELLUNG UND IHRE VERWENDUNG ALS ARZNEIMITTEL
EP0642529B1 (de)	1996-12-11	11beta-substituierte 14,17-ethanoestratriene, verfahren zur herstellung dieser verbindungen, sowie ihre verwendung zur herstellung von arzneimitteln
NZ191899A (en)	1984-11-09	24,24-difluoro-25-hydroxy-vitamin d3 and 24,24-difluoro-25-hydroxy-previtamin d3;pharmaceutical compositions
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