SK282281B6 - 14alfa,17alfa-C2-premostené deriváty 19-nor-progesterónu, farmaceutický prostriedok obsahujúci tieto látky a medziprodukty na ich výrobu - Google Patents
14alfa,17alfa-C2-premostené deriváty 19-nor-progesterónu, farmaceutický prostriedok obsahujúci tieto látky a medziprodukty na ich výrobu Download PDFInfo
- Publication number
- SK282281B6 SK282281B6 SK788-97A SK78897A SK282281B6 SK 282281 B6 SK282281 B6 SK 282281B6 SK 78897 A SK78897 A SK 78897A SK 282281 B6 SK282281 B6 SK 282281B6
- Authority
- SK
- Slovakia
- Prior art keywords
- dione
- ethano
- methyl
- norpregna
- diene
- Prior art date
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- 239000000543 intermediate Substances 0.000 title claims abstract description 15
- 150000000318 19-norprogesterones Chemical class 0.000 title claims abstract description 9
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 title claims abstract 4
- 239000000126 substance Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 254
- 239000003814 drug Substances 0.000 claims abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 83
- 125000004432 carbon atom Chemical group C* 0.000 claims description 81
- 125000000217 alkyl group Chemical group 0.000 claims description 70
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 57
- 229910052739 hydrogen Inorganic materials 0.000 claims description 42
- -1 hydroxyimino Chemical group 0.000 claims description 38
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 36
- 239000001257 hydrogen Substances 0.000 claims description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 19
- 125000006239 protecting group Chemical group 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 12
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 230000036961 partial effect Effects 0.000 claims description 3
- 125000001118 alkylidene group Chemical group 0.000 claims description 2
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- 239000003937 drug carrier Substances 0.000 claims 1
- 230000003152 gestagenic effect Effects 0.000 abstract description 9
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 136
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- 239000003054 catalyst Substances 0.000 description 10
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- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 10
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- UYYCVBASZNFFRX-UHFFFAOYSA-N n-propan-2-ylcyclohexanamine Chemical compound CC(C)NC1CCCCC1 UYYCVBASZNFFRX-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 150000004967 organic peroxy acids Chemical class 0.000 description 1
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229960003387 progesterone Drugs 0.000 description 1
- 239000000186 progesterone Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000001525 receptor binding assay Methods 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 238000006894 reductive elimination reaction Methods 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 102000005969 steroid hormone receptors Human genes 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229940100640 transdermal system Drugs 0.000 description 1
- 238000009901 transfer hydrogenation reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/18—Feminine contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/34—Gestagens
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Gynecology & Obstetrics (AREA)
- Diabetes (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4447401A DE4447401A1 (de) | 1994-12-23 | 1994-12-23 | 14,17-C¶2¶-überbrückte Steroide |
| PCT/EP1995/005107 WO1996020209A2 (de) | 1994-12-23 | 1995-12-23 | 14α,17α-C2-ÜBERBRÜCKTE 19-NOR-PROGESTERONDERIVATE |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK78897A3 SK78897A3 (en) | 1997-12-10 |
| SK282281B6 true SK282281B6 (sk) | 2002-01-07 |
Family
ID=6537601
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK788-97A SK282281B6 (sk) | 1994-12-23 | 1995-12-23 | 14alfa,17alfa-C2-premostené deriváty 19-nor-progesterónu, farmaceutický prostriedok obsahujúci tieto látky a medziprodukty na ich výrobu |
Country Status (33)
| Country | Link |
|---|---|
| US (3) | US5827842A (cs) |
| EP (1) | EP0799238B1 (cs) |
| JP (1) | JPH10511379A (cs) |
| KR (1) | KR100400621B1 (cs) |
| CN (1) | CN1109689C (cs) |
| AR (1) | AR002263A1 (cs) |
| AT (1) | ATE193300T1 (cs) |
| AU (1) | AU692346B2 (cs) |
| BG (1) | BG63274B1 (cs) |
| CA (1) | CA2208605C (cs) |
| CZ (1) | CZ292696B6 (cs) |
| DE (2) | DE4447401A1 (cs) |
| DK (1) | DK0799238T3 (cs) |
| EE (1) | EE03356B1 (cs) |
| ES (1) | ES2151612T3 (cs) |
| FI (1) | FI972624A0 (cs) |
| GR (1) | GR3034261T3 (cs) |
| HU (1) | HUP0600457A2 (cs) |
| IL (1) | IL116504A (cs) |
| LT (1) | LT4295B (cs) |
| LV (1) | LV11954B (cs) |
| NO (1) | NO310198B1 (cs) |
| NZ (1) | NZ298770A (cs) |
| PL (1) | PL182642B1 (cs) |
| PT (1) | PT799238E (cs) |
| RO (1) | RO119366B1 (cs) |
| RU (1) | RU2169153C2 (cs) |
| SI (1) | SI9520137A (cs) |
| SK (1) | SK282281B6 (cs) |
| TW (1) | TW333536B (cs) |
| UA (1) | UA45382C2 (cs) |
| WO (1) | WO1996020209A2 (cs) |
| ZA (1) | ZA9510923B (cs) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU4244997A (en) * | 1996-09-03 | 1998-03-26 | Chugai Seiyaku Kabushiki Kaisha | Intermediates for the synthesis of vitamin d and steroid derivatives and processes for preparation thereof |
| DE19848305C1 (de) * | 1998-10-14 | 2000-05-25 | Schering Ag | Verfahren zur Umsetzung von substituierten Propargylalkoholen in Gegenwart von sauren Ionenaustauschern und Zwischenprodukte des Verfahrens |
| DE19848303A1 (de) * | 1998-10-14 | 2000-04-20 | Schering Ag | Kombination aus Gestagenen und Zuckern |
| EP1216699A1 (de) * | 2000-12-21 | 2002-06-26 | Schering Aktiengesellschaft | Transdermalsystem enthaltend ein hochpotentes Gestagen |
| EP1652526B1 (en) * | 2001-10-26 | 2009-01-14 | N.V. Organon | Use of (11beta, 17beta)-11-(1,3-benzodioxol-5-yl)-17-hydroxy-17-(1-propynyl)-estra-4,9-dien-3-one in the treatment of major depressive disorder |
| DE102007063503A1 (de) | 2007-12-29 | 2009-07-02 | Bayer Schering Pharma Aktiengesellschaft | 17-Hydroxy-19-nor-21-carbonsäure-Steroid y-Lacton-Derivat, dessen Verwendung und das Derivat enthaltende Arzneimittel |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3628189A1 (de) | 1986-08-20 | 1988-02-25 | Schering Ag | Oestrogen wirksame mittel und 14,17ss-ethano-14ss-estratriene |
| DE4326240A1 (de) | 1993-08-02 | 1995-02-09 | Schering Ag | 15,15-Dialkyl-substituierte Derivate des Estradiols |
-
1994
- 1994-12-23 DE DE4447401A patent/DE4447401A1/de not_active Withdrawn
-
1995
- 1995-12-21 ZA ZA9510923A patent/ZA9510923B/xx unknown
- 1995-12-22 AR ARP950100723A patent/AR002263A1/es unknown
- 1995-12-22 IL IL11650495A patent/IL116504A/en not_active IP Right Cessation
- 1995-12-23 PT PT95943195T patent/PT799238E/pt unknown
- 1995-12-23 JP JP8520205A patent/JPH10511379A/ja not_active Ceased
- 1995-12-23 KR KR1019970704251A patent/KR100400621B1/ko not_active Expired - Fee Related
- 1995-12-23 HU HU0600457A patent/HUP0600457A2/hu not_active Application Discontinuation
- 1995-12-23 EE EE9700142A patent/EE03356B1/xx not_active IP Right Cessation
- 1995-12-23 DK DK95943195T patent/DK0799238T3/da active
- 1995-12-23 CA CA002208605A patent/CA2208605C/en not_active Expired - Fee Related
- 1995-12-23 ES ES95943195T patent/ES2151612T3/es not_active Expired - Lifetime
- 1995-12-23 AT AT95943195T patent/ATE193300T1/de not_active IP Right Cessation
- 1995-12-23 AU AU44338/96A patent/AU692346B2/en not_active Ceased
- 1995-12-23 SK SK788-97A patent/SK282281B6/sk unknown
- 1995-12-23 NZ NZ298770A patent/NZ298770A/en unknown
- 1995-12-23 WO PCT/EP1995/005107 patent/WO1996020209A2/de not_active Ceased
- 1995-12-23 CN CN95197047A patent/CN1109689C/zh not_active Expired - Fee Related
- 1995-12-23 RU RU97112100/04A patent/RU2169153C2/ru not_active IP Right Cessation
- 1995-12-23 CZ CZ19971954A patent/CZ292696B6/cs not_active IP Right Cessation
- 1995-12-23 RO RO97-01062A patent/RO119366B1/ro unknown
- 1995-12-23 DE DE59508403T patent/DE59508403D1/de not_active Expired - Fee Related
- 1995-12-23 PL PL95320799A patent/PL182642B1/pl not_active IP Right Cessation
- 1995-12-23 EP EP95943195A patent/EP0799238B1/de not_active Expired - Lifetime
- 1995-12-23 SI SI9520137A patent/SI9520137A/sl not_active IP Right Cessation
- 1995-12-23 UA UA97073911A patent/UA45382C2/uk unknown
- 1995-12-26 US US08/578,847 patent/US5827842A/en not_active Expired - Fee Related
-
1996
- 1996-01-25 TW TW085100899A patent/TW333536B/zh not_active IP Right Cessation
-
1997
- 1997-06-03 BG BG101554A patent/BG63274B1/bg unknown
- 1997-06-18 FI FI972624A patent/FI972624A0/fi unknown
- 1997-06-20 LT LT97-106A patent/LT4295B/lt not_active IP Right Cessation
- 1997-06-20 LV LVP-97-125A patent/LV11954B/lv unknown
- 1997-06-23 NO NO19972927A patent/NO310198B1/no unknown
-
1998
- 1998-08-18 US US09/135,483 patent/US5973172A/en not_active Expired - Fee Related
-
1999
- 1999-07-28 US US09/362,214 patent/US6147065A/en not_active Expired - Fee Related
-
2000
- 2000-08-24 GR GR20000401948T patent/GR3034261T3/el not_active IP Right Cessation
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