NO313554B1 - Antigestagene steroider med en fluorert 17<alfa>-alkylkjede - Google Patents
Antigestagene steroider med en fluorert 17<alfa>-alkylkjede Download PDFInfo
- Publication number
- NO313554B1 NO313554B1 NO19993811A NO993811A NO313554B1 NO 313554 B1 NO313554 B1 NO 313554B1 NO 19993811 A NO19993811 A NO 19993811A NO 993811 A NO993811 A NO 993811A NO 313554 B1 NO313554 B1 NO 313554B1
- Authority
- NO
- Norway
- Prior art keywords
- hydroxy
- pentafluoroethyl
- lip
- group
- denotes
- Prior art date
Links
- 150000003431 steroids Chemical class 0.000 title description 4
- 125000000217 alkyl group Chemical group 0.000 title 1
- 230000000890 antigenic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 66
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
- 230000003637 steroidlike Effects 0.000 claims abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- 239000000825 pharmaceutical preparation Substances 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 3
- 230000001833 anti-estrogenic effect Effects 0.000 claims description 9
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 7
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 230000036961 partial effect Effects 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 1
- -1 hydroxyimino group Chemical group 0.000 abstract description 14
- 238000002360 preparation method Methods 0.000 abstract description 10
- 239000003418 antiprogestin Substances 0.000 abstract description 9
- 230000000694 effects Effects 0.000 abstract description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 abstract 1
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 150000005840 aryl radicals Chemical class 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 abstract 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 105
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 75
- 125000003118 aryl group Chemical group 0.000 description 50
- 239000000203 mixture Substances 0.000 description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 12
- 235000011152 sodium sulphate Nutrition 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 10
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
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- 239000000328 estrogen antagonist Substances 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- UXPOJVLZTPGWFX-UHFFFAOYSA-N pentafluoroethyl iodide Chemical compound FC(F)(F)C(F)(F)I UXPOJVLZTPGWFX-UHFFFAOYSA-N 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
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- 238000001035 drying Methods 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- OMFOGPIVPGTWNN-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4-nonafluorobutane Chemical group F[C](F)C(F)(F)C(F)(F)C(F)(F)F OMFOGPIVPGTWNN-UHFFFAOYSA-N 0.000 description 5
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
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- 201000008275 breast carcinoma Diseases 0.000 description 1
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
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- 229910052744 lithium Inorganic materials 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
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- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
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- 229910052700 potassium Inorganic materials 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0003—Androstane derivatives
- C07J1/0033—Androstane derivatives substituted in position 17 alfa and 17 beta
-
- 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
- A61P15/04—Drugs for genital or sexual disorders; Contraceptives for inducing labour or abortion; Uterotonics
-
- 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
- A61P35/00—Antineoplastic agents
-
- 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
- A61P5/36—Antigestagens
-
- 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
- C07J41/0077—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom
- C07J41/0083—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom substituted in position 11-beta by an optionally substituted phenyl group not further condensed with other rings
-
- 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
- C07J41/0094—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 containing nitrile radicals, including thiocyanide radicals
-
- 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
- C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Endocrinology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Reproductive Health (AREA)
- Gynecology & Obstetrics (AREA)
- Toxicology (AREA)
- Diabetes (AREA)
- Pregnancy & Childbirth (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19706061A DE19706061A1 (de) | 1997-02-07 | 1997-02-07 | Antigestagen wirksame Steroide mit fluorierter 17alpha-Alkylkette |
| PCT/EP1998/000752 WO1998034947A1 (de) | 1997-02-07 | 1998-02-09 | ANTIGESTAGEN WIRKSAME STEROIDE MIT FLUORIERTER 17α-ALKYLKETTE |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO993811D0 NO993811D0 (no) | 1999-08-06 |
| NO993811L NO993811L (no) | 1999-10-04 |
| NO313554B1 true NO313554B1 (no) | 2002-10-21 |
Family
ID=7820508
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19993811A NO313554B1 (no) | 1997-02-07 | 1999-08-06 | Antigestagene steroider med en fluorert 17<alfa>-alkylkjede |
Country Status (35)
| Country | Link |
|---|---|
| US (4) | US6316432B1 (zh) |
| EP (1) | EP0970103B1 (zh) |
| JP (1) | JP4324249B2 (zh) |
| KR (1) | KR100511815B1 (zh) |
| CN (2) | CN1246865A (zh) |
| AR (1) | AR010887A1 (zh) |
| AT (1) | ATE216397T1 (zh) |
| AU (1) | AU742834B2 (zh) |
| BG (1) | BG63875B1 (zh) |
| BR (1) | BR9807667A (zh) |
| CA (1) | CA2280041C (zh) |
| CL (1) | CL2004001191A1 (zh) |
| CZ (1) | CZ296328B6 (zh) |
| DE (2) | DE19706061A1 (zh) |
| DK (1) | DK0970103T3 (zh) |
| EA (1) | EA003092B1 (zh) |
| EE (1) | EE03831B1 (zh) |
| ES (1) | ES2175673T3 (zh) |
| HK (1) | HK1040718B (zh) |
| HU (1) | HUP0000968A3 (zh) |
| ID (1) | ID22643A (zh) |
| IL (1) | IL131226A (zh) |
| IS (1) | IS2190B (zh) |
| MY (1) | MY118508A (zh) |
| NO (1) | NO313554B1 (zh) |
| NZ (1) | NZ336989A (zh) |
| PL (1) | PL191808B1 (zh) |
| PT (1) | PT970103E (zh) |
| SI (1) | SI0970103T1 (zh) |
| SK (1) | SK283155B6 (zh) |
| TR (1) | TR199901855T2 (zh) |
| TW (1) | TW499434B (zh) |
| UA (1) | UA66783C2 (zh) |
| WO (1) | WO1998034947A1 (zh) |
| ZA (1) | ZA98985B (zh) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19706061A1 (de) * | 1997-02-07 | 1998-08-13 | Schering Ag | Antigestagen wirksame Steroide mit fluorierter 17alpha-Alkylkette |
| DE10049736A1 (de) * | 2000-09-29 | 2002-04-18 | Jenapharm Gmbh | 17alpha-Fluoralkylsteroide, Verfahren zu deren Herstellung und diese Verbindungen enthaltende pharmazeutische Zusammensetzungen |
| DE10051609A1 (de) * | 2000-10-18 | 2002-05-02 | Schering Ag | Hemmung der Wachstumsfaktorabhängigkeit von Tumorzellen |
| UY26965A1 (es) * | 2000-10-18 | 2002-06-20 | Schering Ag | Uso de antiprogestinas para la profilaxis y el tratamiento de enfermedades dependientes de hormonas |
| PL366415A1 (en) * | 2000-10-18 | 2005-01-24 | Schering Aktiengesellschaft | Inhibition of the growth factor dependency of tumor cells |
| UY26966A1 (es) * | 2000-10-18 | 2002-06-20 | Schering Ag | Uso de antiprogestinas para la inducción de apoptosis en una célula |
| UA76729C2 (uk) * | 2000-10-18 | 2006-09-15 | Шерінг Акцієнгезельшафт | ЗАСТОСУВАННЯ АНТИПРОГЕСТИНУ 11<font face="Symbol">b</font>-(4-АЦЕТИЛФЕНІЛ)-17<font face="Symbol">b</font>-ГІДРОКСИ-17<font face="Symbol">a</font>-(1,1,2,2,2-ПЕНТАФТОРЕТИЛ)ЕСТРА-4,9-ДІЄН-3-ОНУ ДЛЯ ЛІКУВАННЯ РАКУ ШЛЯХОМ ІНДУКУВАННЯ АПОПТОЗУ КЛІТИНИ |
| JP2004511522A (ja) * | 2000-10-18 | 2004-04-15 | シエーリング アクチエンゲゼルシャフト | ホルモン−依存性疾病の予防及び処理のための抗黄体ホルモンの使用 |
| PL361689A1 (en) * | 2001-01-09 | 2004-10-04 | Schering Aktiengesellschaft | The use of antigestagens for inhibiting accelerated endometrial maturation during infertility treatment |
| US20020143000A1 (en) * | 2001-01-09 | 2002-10-03 | Christa Hegele-Hartung | Use of antigestagens for inhibiting accelerated endometrial maturation during infertility treatment |
| UY27301A1 (es) * | 2001-05-25 | 2003-02-28 | Schering Ag | Uso y composiciones de antiprogestinas para el tratamiento de enfermedades de la próstata |
| US20030013694A1 (en) * | 2001-05-25 | 2003-01-16 | Jens Hoffmann | Use and compositions of antiprogestins for treatment of prostate diseases |
| DE10159217A1 (de) | 2001-11-27 | 2003-06-05 | Schering Ag | 17alpha-Alkyl-17ß-oxy-estratriene und Zwischenprodukte zu deren Herstellung, Verwendung der 17alpha-Alkyl-17ß-oxy-estratriene zur Herstellung von Arzneimitteln sowie pharmazeutische Präparate |
| DE10221034A1 (de) * | 2002-05-03 | 2003-11-20 | Schering Ag | 17alpha-Fluoralkyl-11ß-benzaldoxim-Steroide, Verfahren zu deren Herstellung, diese Steroide enthaltende pharmazeutische Präparate sowie deren Verwendung zur Herstellung von Arzneimitteln |
| JP2005536463A (ja) * | 2002-05-03 | 2005-12-02 | シエーリング アクチエンゲゼルシャフト | １７α−フルオロアルキル−１１β−ベンズアルドキシムステロイド、それらの製造方法、これらのステロイド類を含有する製剤及び医薬品製造のためのそれらの使用 |
| US20040242551A1 (en) * | 2003-05-28 | 2004-12-02 | Schering Ag | Composition comprising antiprogestins and pure antiestrogens for prophylaxis and treatment of hormone-dependent diseases |
| NZ580384A (en) | 2003-07-23 | 2011-03-31 | Bayer Pharmaceuticals Corp | 4{4-[3-(4-chloro-3-trifluoromethylphenyl)-ureido]-3-fluorophenoxy}-pyridine-2-carboxylic acid methylamide and metabolites for the treatment and prevention of diseases and conditions |
| US7593347B2 (en) * | 2003-12-29 | 2009-09-22 | Intel Corporation | Method and apparatus to exchange channel information |
| EP1862468A1 (de) * | 2006-06-02 | 2007-12-05 | Bayer Schering Pharma Aktiengesellschaft | Kristallines 11beta-(4-Acetylphenyl)-20,20,21,21,21-pentafluor-17-hydroxy-19-nor-17alpha-pregna-4,9-dien-3-on |
| EP3693376A1 (en) | 2006-10-24 | 2020-08-12 | Allergan Pharmaceuticals International Limited | Compositions for suppressing endometrial proliferation |
| DE102006054535A1 (de) | 2006-11-15 | 2008-05-21 | Bayer Schering Pharma Aktiengesellschaft | Progesteronrezeptorantagonisten |
| US20080268041A1 (en) * | 2007-04-23 | 2008-10-30 | Jens Hoffmann | Combination of progesterone-receptor antagonist together with none-steroidal antiestrogen for use in brca mediated diseases |
| JP2010524997A (ja) * | 2007-04-23 | 2010-07-22 | バイエル・シエーリング・ファーマ アクチエンゲゼルシャフト | Ｂｒｃａ単独での、又は抗エストロゲン薬を伴った組み合わせ物としての使用のためのプロゲステロン受容体拮抗薬 |
| TWI539953B (zh) | 2008-04-28 | 2016-07-01 | 瑞波若斯治療學公司 | 用於治療乳癌之組成物和方法 |
| EP2123279A1 (de) * | 2008-05-14 | 2009-11-25 | Bayer Schering Pharma Aktiengesellschaft | Sequentielle Verabreichung von 20,20,21,21,21-Pentafluor-17-hydroxy-1 1beta-[4-(hydroxyacetyl) phenyl]-19-nor-17alpha-pregna-4,9-dien-3-on und einem oder mehreren Gestagenen zur Behandlung gynäkologischer Erkrankungen |
| US20100087402A1 (en) * | 2008-09-29 | 2010-04-08 | Vivus, Inc. | Methods and compositions for the treatment of estrogen-dependent hyperproliferative uterine disorders |
| DE102009034366A1 (de) | 2009-07-20 | 2011-01-27 | Bayer Schering Pharma Aktiengesellschaft | 17-Hydroxy-17-pentafluorethyl-estra-4,9(10)-dien-11-methylenoxyalkylenaryl-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Behandlung von Krankheiten |
| DE102009034362A1 (de) * | 2009-07-20 | 2011-01-27 | Bayer Schering Pharma Aktiengesellschaft | 17-Hydroxy-17-pentafluorethyl-estra-4,9(10)-dien-11-aryl-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Behandlung von Krankheiten |
| DE102009034368A1 (de) | 2009-07-20 | 2011-01-27 | Bayer Schering Pharma Aktiengesellschaft | 17-Hydroxy-17-pentafluorethyl-estra-4,9(10)-dien-11-acyloxyalkylenphenyl-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Behandlung von Krankheiten |
| DE102009034367A1 (de) | 2009-07-20 | 2011-01-27 | Bayer Schering Pharma Aktiengesellschaft | 17-Hydroxy-17-pentafluorethyl-estra-4,9(10)-dien-11-benzyliden-Derivate, Verfahren zu deren Herstellung und deren Verwendung zur Behandlung von Krankheiten |
| DE102009034525A1 (de) | 2009-07-21 | 2011-01-27 | Bayer Schering Pharma Aktiengesellschaft | 17-Hydroxy-17-pentafluorethyl-estra-4,9(10)-dien-11-aryl-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Behandlung von Krankheiten |
| DE102009034526A1 (de) | 2009-07-21 | 2011-02-10 | Bayer Schering Pharma Aktiengesellschaft | 17-Hydroxy-17-pentafluorethyl-estra-4,9(10)-dien-11-ethinylphenyl-Derivate, Verfahren zu deren Herstellung und deren Verwendung zur Behandlung von Krankheiten |
| DE102010007719A1 (de) | 2010-02-10 | 2011-08-11 | Bayer Schering Pharma Aktiengesellschaft, 13353 | Progesteronrezeptorantagonisten |
| DE102010007722A1 (de) | 2010-02-10 | 2011-08-11 | Bayer Schering Pharma Aktiengesellschaft, 13353 | Progesteronrezeptorantagonisten |
| WO2011119194A1 (en) | 2010-03-22 | 2011-09-29 | Repros Therapeutics Inc. | Compositions and methods for non-toxic delivery of antiprogestins |
| DE102010030538A1 (de) | 2010-06-25 | 2011-12-29 | Bayer Schering Pharma Aktiengesellschaft | 6,7-Dihydro-5H-benzo[7]annulen-Derivate, Verfahren zu ihrer Herstellung, pharmazeutische Präparate die diese enthalten, sowie deren Verwendung zur Herstellung von Arzneimitteln |
| DE102011004899A1 (de) | 2011-03-01 | 2012-09-06 | Bayer Pharma Aktiengesellschaft | 17-Hydroxy-17-pentafluorethyl-estra-4,9(10)-dien-11-aryl-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Behandlung von Krankheiten |
| US20130029953A1 (en) * | 2011-07-28 | 2013-01-31 | Klaus Nickisch | Progesterone antagonists |
| DE102011087987A1 (de) | 2011-12-08 | 2013-06-13 | Bayer Intellectual Property Gmbh | 6,7-Dihydro-5H-benzo[7]annulen-Derivate, Verfahren zu ihrer Herstellung, pharmazeutische Präparate die diese enthalten, sowie deren Verwendung zur Herstellung von Arzneimitteln |
| EP2983671B1 (en) | 2013-04-11 | 2018-10-24 | Bayer Pharma Aktiengesellschaft | Progesterone receptor antagonist dosage form |
| US9096641B2 (en) | 2013-06-05 | 2015-08-04 | Evestra, Inc. | Imidazolyl progesterone antagonists |
| EP2868321A1 (en) | 2013-11-03 | 2015-05-06 | Flamina Holding AG | A composition or group of compositions for inhibiting autocrine HCG production in adult human cells |
| US9603856B2 (en) | 2013-11-03 | 2017-03-28 | Flamina Holding Ag | Pharmaceutical composition or group of compositions for inhibiting autocrine HCG production in adult human cells |
| CN107635562A (zh) | 2015-05-18 | 2018-01-26 | 拜耳医药股份有限公司 | 选择性孕酮受体调节剂（sprm）方案 |
| EP3214092A1 (en) | 2016-03-04 | 2017-09-06 | Bayer Pharma Aktiengesellschaft | Prodrugs of the selective progesterone receptor modulator (sprm) (11.beta.,17.beta.)-17-hydroxy-11-[4-(methylsulphonyl)phenyl]-17-(pentafluoroethyl)estra-4,9-dien-3-one |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE310541C (zh) * | 1915-12-19 | 1919-01-30 | ||
| ZA8231B (en) * | 1981-01-09 | 1982-11-24 | Roussel Uclaf | New 11 -substituted steroid derivatives, their preparation, their use as medicaments, the compositions containing them and the new intermediates thus obtained |
| FR2639045B2 (fr) | 1982-03-01 | 1994-07-29 | Roussel Uclaf | Nouveaux produits derives de la structure 3-ceto-delta-4,9-19-nor steroides et leur application comme medicaments |
| US5064821A (en) * | 1982-11-18 | 1991-11-12 | Trustees Of Tufts College | Method and compositions for overcoming tetracycline resistance within living cells |
| FR2598421B1 (fr) * | 1986-05-06 | 1988-08-19 | Roussel Uclaf | Nouveaux produits 19-nor ou 19-nor d-homo steroides substitues en position 11b par un radical phenyle portant un radical alkynyle, leur procede de preparation, leur application comme medicaments et les compositions les renfermant |
| US5272140A (en) * | 1987-01-23 | 1993-12-21 | Akzo N.V. | 11-aryl steroid derivatives |
| DE3723788A1 (de) * | 1987-07-16 | 1989-01-26 | Schering Ag | 11(beta)-phenyl-4,9,15-estratriene, deren herstellung und diese enthaltende pharmazeutische praeparate |
| DE3733478A1 (de) | 1987-10-01 | 1989-04-13 | Schering Ag | Antigestagen- und antioestrogenwirksame verbindungen zur geburtseinleitung und zum schwangerschaftsabbruch sowie zur behandlung gynaekologischer stoerungen und hormonabhaengiger tumore |
| BE1004905A4 (fr) * | 1987-12-30 | 1993-02-23 | Roussel Uclaf | Nouveaux derives 17beta-oh 19-nor steroides substitues en 17alpha, leur procede de preparation, leur application comme medicaments et les compositions pharmaceutiques les renfermant. |
| EP0369881A1 (fr) * | 1988-11-16 | 1990-05-23 | Roussel-Uclaf | Nouveaux produits dérivés de la structure 3-céto delta-4,9 19-nor stéroides et leur application comme médicaments |
| DE3921059A1 (de) * | 1989-06-23 | 1991-01-10 | Schering Ag | 11(beta)-aryl-4-estrene, verfahren zu ihrer herstellung sowie deren verwendung als arzneimittel |
| CN1055929C (zh) * | 1993-09-20 | 2000-08-30 | 中国科学院上海有机化学研究所 | 三氟甲基甾体化合物及其制备方法 |
| DE19706061A1 (de) * | 1997-02-07 | 1998-08-13 | Schering Ag | Antigestagen wirksame Steroide mit fluorierter 17alpha-Alkylkette |
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- 1998-02-09 WO PCT/EP1998/000752 patent/WO1998034947A1/de active IP Right Grant
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