FI65785C - Foerfarande foer framstaellning av terapeutiskt anvaendbara sustituerade steroid-spiro-oxazolidinon-derivat - Google Patents

Foerfarande foer framstaellning av terapeutiskt anvaendbara sustituerade steroid-spiro-oxazolidinon-derivat Download PDF

Info

Publication number: FI65785C
Authority: FI; Finland
Prior art keywords: group; hydrogen atom; betecknar; spiro; och
Prior art date: 1978-04-01

Application number

FI791051A

Other languages

English (en)

Finnish (fi)

Other versions

FI791051A7 (fi

FI65785B (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.)

1978-04-01

Filing date

1979-03-29

Publication date

1984-07-10

1979-03-29 Application filed by Richter Gedeon Vegyeszet filed Critical Richter Gedeon Vegyeszet

1979-10-02 Publication of FI791051A7 publication Critical patent/FI791051A7/fi

1984-03-30 Application granted granted Critical

1984-03-30 Publication of FI65785B publication Critical patent/FI65785B/fi

1984-07-10 Publication of FI65785C publication Critical patent/FI65785C/fi

Links

150000001875 compounds Chemical class 0.000 claims description 20
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
238000000034 method Methods 0.000 claims description 12
238000002360 preparation method Methods 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 3
125000002252 acyl group Chemical group 0.000 claims description 2
150000003573 thiols Chemical class 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
101100426973 Caenorhabditis elegans ttr-3 gene Proteins 0.000 claims 1
125000001424 substituent group Chemical group 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
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 8
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
-1 alkyl mercaptan Chemical compound 0.000 description 5
239000012043 crude product Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 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
239000000047 product 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
241000700159 Rattus Species 0.000 description 3
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 3
229960002478 aldosterone Drugs 0.000 description 3
229940083712 aldosterone antagonist Drugs 0.000 description 3
239000002170 aldosterone antagonist Substances 0.000 description 3
230000001833 anti-estrogenic effect Effects 0.000 description 3
229960004486 desoxycorticosterone acetate Drugs 0.000 description 3
210000004907 gland Anatomy 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
150000003431 steroids Chemical class 0.000 description 3
239000000126 substance Substances 0.000 description 3
229960001712 testosterone propionate Drugs 0.000 description 3
230000001836 utereotrophic effect Effects 0.000 description 3
238000005303 weighing Methods 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
210000004100 adrenal gland Anatomy 0.000 description 2
230000002280 anti-androgenic effect Effects 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
230000002124 endocrine Effects 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000011160 research Methods 0.000 description 2
239000011734 sodium Substances 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
208000009447 Cardiac Edema Diseases 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
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 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
206010030113 Oedema Diseases 0.000 description 1
208000004880 Polyuria Diseases 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
239000013543 active substance Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
210000004404 adrenal cortex Anatomy 0.000 description 1
230000001864 anti-aldosterone effect Effects 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
230000036765 blood level Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
238000011161 development Methods 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
239000000328 estrogen antagonist Substances 0.000 description 1
230000029142 excretion Effects 0.000 description 1
238000005048 flame photometry Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
210000002149 gonad Anatomy 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000002440 hepatic effect Effects 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 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
210000003734 kidney Anatomy 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 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
230000001575 pathological effect Effects 0.000 description 1
230000007170 pathology Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
201000009395 primary hyperaldosteronism Diseases 0.000 description 1
210000002307 prostate Anatomy 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
230000028327 secretion Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910001415 sodium ion Inorganic materials 0.000 description 1
239000002904 solvent Substances 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
238000003756 stirring 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
238000012360 testing method Methods 0.000 description 1
238000001665 trituration Methods 0.000 description 1
230000002485 urinary effect Effects 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)

FI791051A 1978-04-01 1979-03-29 Foerfarande foer framstaellning av terapeutiskt anvaendbara sustituerade steroid-spiro-oxazolidinon-derivat FI65785C (fi)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HUGO001397		1978-04-01
HU78GO1397A HU178397B (en)	1978-04-01	1978-04-01	Process for preparing substituted derivatives of steroid-spiro-oxazolidione derivatives

Publications (3)

Publication Number	Publication Date
FI791051A7 FI791051A7 (fi)	1979-10-02
FI65785B FI65785B (fi)	1984-03-30
FI65785C true FI65785C (fi)	1984-07-10

Family

ID=10996851

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI791051A FI65785C (fi)	1978-04-01	1979-03-29	Foerfarande foer framstaellning av terapeutiskt anvaendbara sustituerade steroid-spiro-oxazolidinon-derivat

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
US7732432B2 (en) *	2003-01-21	2010-06-08	Merck Sharp & Dohme Corp.	17-carbamoyloxy cortisol derivatives as selective glucocorticoid receptor modulators
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 SE SE7902788A patent/SE7902788L/xx not_active Application Discontinuation
- 1979-03-28 FR FR7907741A patent/FR2421181A1/fr active Granted
- 1979-03-28 YU YU00735/79A patent/YU73579A/xx unknown
- 1979-03-29 SU SU792744750A patent/SU852176A3/ru active
- 1979-03-29 FI FI791051A patent/FI65785C/fi not_active IP Right Cessation
- 1979-03-29 US US06/025,080 patent/US4218446A/en not_active Expired - Lifetime
- 1979-03-30 IT IT21432/79A patent/IT1113203B/it active
- 1979-03-30 AU AU45648/79A patent/AU523226B2/en not_active Ceased
- 1979-03-30 DK DK131379A patent/DK131379A/da not_active Application Discontinuation
- 1979-03-30 DE DE19792912835 patent/DE2912835A1/de not_active Withdrawn
- 1979-03-30 NO NO791059A patent/NO791059L/no unknown
- 1979-03-30 JP JP3829879A patent/JPS54132565A/ja active Pending
- 1979-03-30 GB GB7911132A patent/GB2017708B/en not_active Expired
- 1979-03-30 CA CA000324686A patent/CA1118767A/en not_active Expired
- 1979-03-30 NL NL7902528A patent/NL7902528A/xx not_active Application Discontinuation
- 1979-03-30 CH CH296379A patent/CH640247A5/de not_active IP Right Cessation
- 1979-03-31 ES ES479170A patent/ES479170A1/es not_active Expired

Also Published As

Publication number	Publication date
CH640247A5 (de)	1983-12-30
AT366392B (de)	1982-04-13
JPS54132565A (en)	1979-10-15
YU73579A (en)	1982-10-31
US4218446A (en)	1980-08-19
DK131379A (da)	1979-10-02
SE7902788L (sv)	1979-10-02
FR2421181B1 (de)	1982-10-22
IT7921432A0 (it)	1979-03-30
IL56913A0 (en)	1979-05-31
FI791051A7 (fi)	1979-10-02
BE875091A (fr)	1979-09-26
IL56913A (en)	1982-08-31
FI65785B (fi)	1984-03-30
NO791059L (no)	1979-10-02
FR2421181A1 (fr)	1979-10-26
IT1113203B (it)	1986-01-20
GB2017708B (en)	1982-10-27
NL7902528A (nl)	1979-10-03
ES479170A1 (es)	1979-07-01
GB2017708A (en)	1979-10-10
AU4564879A (en)	1979-10-25
AU523226B2 (en)	1982-07-15
HU178397B (en)	1982-04-28
CA1118767A (en)	1982-02-23
ATA213579A (de)	1981-08-15
SU852176A3 (ru)	1981-07-30
DE2912835A1 (de)	1979-10-11

Legal Events

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

Publication	Publication Date	Title
CELLA et al.	1959	Steroidal aldosterone blockers. II1
EP0004648B1 (de)	1982-08-25	Neue Mercaptoimidazolderivate, Verfahren zu deren Herstellung, Mercaptoimidazolderivate zur Behandlung entzündlicher Erkrankungen und diese enthaltende pharmazeutische Präparate
DD145538A5 (de)	1980-12-17	Verfahren zur herstellung von bicyclischen thia-diaza-verbindungen
US4218446A (en)	1980-08-19	Substituted steroid-spiro-oxazolidinone derivatives and a process for the preparation thereof
DE2405395A1 (de)	1974-08-15	Verfahren zur herstellung von neuen azinen und ihren tautomeren
EP0546591A2 (de)	1993-06-16	11-Beta-Substituierte 14,17-Ethanoestratriene, Verfahren zur Herstellung dieser Verbindungen sowie ihre Verwendung zur Herstellung von Arzneimitteln
US4328221A (en)	1982-05-04	Substituted steroid-spiro-oxazolidinone derivatives and a process for the preparation thereof
EP0410554A2 (de)	1991-01-30	14,17 alfa-Ethano- und Ethanoestratriene, Verfahren zur Herstellung dieser Verbindungen, sowie ihre Verwendung zur Herstellung von Arzneimitteln
US4331663A (en)	1982-05-25	4α,5α-Epoxy-3,20-dioxopregnane-2α,16α-dicarbonitrile and intermediates and process for preparation, method of use and compositions thereof
EP0213295B1 (de)	1991-04-10	Neue Thieno-1,2-thiazolderivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
SE446338B (sv)	1986-09-01	2-hydroximetyl-pyrazin-4-oxid-derivat, forfarande for framstellning derav samt farmaceutisk komposition innehallande dessa derivat
EP0013955A1 (de)	1980-08-06	Neue Analoga von Prostacyclin, deren Zwischenprodukte, Verfahren zu ihrer Herstellung sowie sie enthaltende Arzneimittel
PL127257B1 (en)	1983-10-31	Method of obtaining 1-substituted-3-cycloalkylo-sulphonylo-pyrrolidino-2,5-diones
DE3438244A1 (de)	1985-04-25	4-chlor-furo-(3,4-c)-pyridinderivate, verfahren zu ihrer herstellung und arzneimittel mit einem gehalt an diesen verbindungen
EP0004335A2 (de)	1979-10-03	Neue Analoga von Prostacyclin, Verfahren und Zwischenprodukte zu ihrer Herstellung und ihre Verwendung als Arzneimittel
IE42419B1 (en)	1980-07-30	Triazolobenzocycloalkylthiadiazine derivatives
EP0014966B1 (de)	1985-06-05	Neue deA-Steroide, ihre Herstellung und deA-Steroide zur Verwendung als Pharmazeutika
EP0193871A2 (de)	1986-09-10	2-Oxa- oder -Aza-Pregnanderivate
US3931172A (en)	1976-01-06	1-Tertiary-butyl-3-morpholino-3-phenyl-2,1-benzisoxaxolines
US3499965A (en)	1970-03-10	7alpha - lower alkylthio - 17beta - hydroxy - 17alpha- methyl - 5alpha - androstano(3,2 - c)pyrazole and novel intermediates useful in the preparation thereof
EP0244833B1 (de)	1992-06-24	4(R)-substituierte 6(S)-Phenoxymethyl-, 6(S)-beta-Phenyläthyl- und 6(S)-beta-Styryl-tetrahydropyran-2-one, ein hochstereoselektives Verfahren zu ihrer Herstellung, pharmazeutische Präparate auf Basis dieser Verbindungen und ihre Verwendung
US3366654A (en)	1968-01-30	17-alkoxyalkyl and hydroxyalkyl ethers of 3-substituted-1, 3, 5(10) estratrienes
US3511871A (en)	1970-05-12	Glycyrrhetinic acid derivatives
EP0006971B1 (de)	1981-12-02	Aminoderivate des 2-Methyl-5-(2-hydroxystyryl)-1,3,4-thiadiazols, Verfahren zu ihrer Herstellung und diese enthaltende therapeutische Mittel
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