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 PDFInfo
- Publication number
- FI65785C FI65785C FI791051A FI791051A FI65785C FI 65785 C FI65785 C FI 65785C FI 791051 A FI791051 A FI 791051A FI 791051 A FI791051 A FI 791051A FI 65785 C FI65785 C FI 65785C
- Authority
- FI
- Finland
- Prior art keywords
- group
- hydrogen atom
- betecknar
- spiro
- och
- Prior art date
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)
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 (da) |
| JP (1) | JPS54132565A (da) |
| AT (1) | AT366392B (da) |
| AU (1) | AU523226B2 (da) |
| BE (1) | BE875091A (da) |
| CA (1) | CA1118767A (da) |
| CH (1) | CH640247A5 (da) |
| DE (1) | DE2912835A1 (da) |
| DK (1) | DK131379A (da) |
| ES (1) | ES479170A1 (da) |
| FI (1) | FI65785C (da) |
| FR (1) | FR2421181A1 (da) |
| GB (1) | GB2017708B (da) |
| HU (1) | HU178397B (da) |
| IL (1) | IL56913A (da) |
| IT (1) | IT1113203B (da) |
| NL (1) | NL7902528A (da) |
| NO (1) | NO791059L (da) |
| SE (1) | SE7902788L (da) |
| SU (1) | SU852176A3 (da) |
| YU (1) | YU73579A (da) |
Families Citing this family (7)
| 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 (da) * | 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 |
| CA2512987C (en) * | 2003-01-21 | 2011-06-14 | Merck & Co., Inc. | 17-carbamoyloxy cortisol derivatives as selective glucocorticoid receptor modulators |
| WO2007025780A2 (en) * | 2005-09-02 | 2007-03-08 | Recordati Ireland Limited | Aldosterone receptor antagonists |
| CN117858887A (zh) * | 2021-06-16 | 2024-04-09 | 拉瓦勒大学 | 17β-HSD7的新型抑制剂及其用途 |
Family Cites Families (3)
| 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 SE SE7902788A patent/SE7902788L/xx not_active Application Discontinuation
- 1979-03-28 YU YU00735/79A patent/YU73579A/xx unknown
- 1979-03-29 FI FI791051A patent/FI65785C/fi not_active IP Right Cessation
- 1979-03-29 SU SU792744750A patent/SU852176A3/ru active
- 1979-03-29 US US06/025,080 patent/US4218446A/en not_active Expired - Lifetime
- 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 CH CH296379A patent/CH640247A5/de not_active IP Right Cessation
- 1979-03-30 NO NO791059A patent/NO791059L/no unknown
- 1979-03-30 DE DE19792912835 patent/DE2912835A1/de not_active Withdrawn
- 1979-03-30 CA CA000324686A patent/CA1118767A/en not_active Expired
- 1979-03-30 IT IT21432/79A patent/IT1113203B/it active
- 1979-03-30 JP JP3829879A patent/JPS54132565A/ja active Pending
- 1979-03-30 GB GB7911132A patent/GB2017708B/en not_active Expired
- 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 |
|---|---|
| DE2912835A1 (de) | 1979-10-11 |
| BE875091A (fr) | 1979-09-26 |
| US4218446A (en) | 1980-08-19 |
| YU73579A (en) | 1982-10-31 |
| HU178397B (en) | 1982-04-28 |
| SE7902788L (sv) | 1979-10-02 |
| FI65785B (fi) | 1984-03-30 |
| CH640247A5 (de) | 1983-12-30 |
| DK131379A (da) | 1979-10-02 |
| NL7902528A (nl) | 1979-10-03 |
| ES479170A1 (es) | 1979-07-01 |
| AU4564879A (en) | 1979-10-25 |
| IL56913A (en) | 1982-08-31 |
| FI791051A7 (fi) | 1979-10-02 |
| CA1118767A (en) | 1982-02-23 |
| NO791059L (no) | 1979-10-02 |
| AU523226B2 (en) | 1982-07-15 |
| GB2017708B (en) | 1982-10-27 |
| IT1113203B (it) | 1986-01-20 |
| IL56913A0 (en) | 1979-05-31 |
| IT7921432A0 (it) | 1979-03-30 |
| FR2421181B1 (da) | 1982-10-22 |
| AT366392B (de) | 1982-04-13 |
| SU852176A3 (ru) | 1981-07-30 |
| FR2421181A1 (fr) | 1979-10-26 |
| GB2017708A (en) | 1979-10-10 |
| ATA213579A (de) | 1981-08-15 |
| JPS54132565A (en) | 1979-10-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: RICHTER GEDEON VEGYESZETI GYAR RT. |