CA2119780A1 - 11.beta.-substituted 14,17-ethanoestratrienes, process for preparing these compounds and their use for preparing medicaments - Google Patents
11.beta.-substituted 14,17-ethanoestratrienes, process for preparing these compounds and their use for preparing medicamentsInfo
- Publication number
- CA2119780A1 CA2119780A1 CA002119780A CA2119780A CA2119780A1 CA 2119780 A1 CA2119780 A1 CA 2119780A1 CA 002119780 A CA002119780 A CA 002119780A CA 2119780 A CA2119780 A CA 2119780A CA 2119780 A1 CA2119780 A1 CA 2119780A1
- Authority
- CA
- Canada
- Prior art keywords
- ethano
- acid
- methyl
- amide
- trien
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 28
- CWTQJAXOSASVNU-ONCXSQPRSA-N C([C@@H]12)CCCC1=CC=C1[C@@H]2CC[C@@]2(C)[C@@]11CC=C2CC1 Chemical class C([C@@H]12)CCCC1=CC=C1[C@@H]2CC[C@@]2(C)[C@@]11CC=C2CC1 CWTQJAXOSASVNU-ONCXSQPRSA-N 0.000 title claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 239000003814 drug Substances 0.000 title abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 8
- 239000000825 pharmaceutical preparation Substances 0.000 claims abstract description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 25
- 239000002253 acid Substances 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 8
- 150000008065 acid anhydrides Chemical class 0.000 claims description 7
- 150000004820 halides Chemical class 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 239000008177 pharmaceutical agent Substances 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000000468 ketone group Chemical group 0.000 claims description 3
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 75
- 239000000243 solution Substances 0.000 description 58
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 27
- 229910052938 sodium sulfate Inorganic materials 0.000 description 27
- 235000011152 sodium sulphate Nutrition 0.000 description 27
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 26
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 235000002639 sodium chloride Nutrition 0.000 description 23
- 239000011780 sodium chloride Substances 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 239000003921 oil Substances 0.000 description 16
- 235000019198 oils Nutrition 0.000 description 16
- 239000000741 silica gel Substances 0.000 description 16
- 229910002027 silica gel Inorganic materials 0.000 description 16
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- 230000008020 evaporation Effects 0.000 description 15
- 238000001704 evaporation Methods 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 235000017557 sodium bicarbonate Nutrition 0.000 description 11
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
- -1 methylcyclopentyl group Chemical group 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- QROUUECTKRZFHF-UHFFFAOYSA-N 4,4,5,5,5-pentafluoropentan-1-ol Chemical compound OCCCC(F)(F)C(F)(F)F QROUUECTKRZFHF-UHFFFAOYSA-N 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000006260 foam Substances 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- FXXACINHVKSMDR-UHFFFAOYSA-N acetyl bromide Chemical compound CC(Br)=O FXXACINHVKSMDR-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 239000002671 adjuvant Substances 0.000 description 4
- 230000001833 anti-estrogenic effect Effects 0.000 description 4
- XHFGWHUWQXTGAT-UHFFFAOYSA-N n-methylpropan-2-amine Chemical compound CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 4
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- OLHXONQUABFOJU-UHFFFAOYSA-N 11-bromoundecoxy-tert-butyl-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)OCCCCCCCCCCCBr OLHXONQUABFOJU-UHFFFAOYSA-N 0.000 description 3
- OZRFWLLFSGXBOH-UHFFFAOYSA-N 4,4,5,5,5-pentafluoropentane-1-thiol Chemical compound FC(F)(F)C(F)(F)CCCS OZRFWLLFSGXBOH-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229940046836 anti-estrogen Drugs 0.000 description 3
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000000328 estrogen antagonist Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- WWAZGZHGMUGDNB-OWOJBTEDSA-N (e)-4,4,5,5,5-pentafluoropent-2-en-1-ol Chemical compound OC\C=C\C(F)(F)C(F)(F)F WWAZGZHGMUGDNB-OWOJBTEDSA-N 0.000 description 2
- GDEVQDVVXJLJOX-UHFFFAOYSA-N 1-bromo-9-(4,4,5,5,5-pentafluoropentylsulfanyl)nonane Chemical compound FC(F)(F)C(F)(F)CCCSCCCCCCCCCBr GDEVQDVVXJLJOX-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000003810 Jones reagent Substances 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 230000001076 estrogenic effect Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000007943 implant Substances 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- KHEUHEBTOQSOSU-UHFFFAOYSA-N s-(4,4,5,5,5-pentafluoropentyl) ethanethioate Chemical compound CC(=O)SCCCC(F)(F)C(F)(F)F KHEUHEBTOQSOSU-UHFFFAOYSA-N 0.000 description 2
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 2
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- SRYOTJAZYZLPMY-UHFFFAOYSA-N 10-bromodecoxy-tert-butyl-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)OCCCCCCCCCCBr SRYOTJAZYZLPMY-UHFFFAOYSA-N 0.000 description 1
- NFUQZVUAJDEGGF-UHFFFAOYSA-N 12-bromododecoxy-tert-butyl-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)OCCCCCCCCCCCCBr NFUQZVUAJDEGGF-UHFFFAOYSA-N 0.000 description 1
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 1
- XODUVTJXUOOAKV-UHFFFAOYSA-N 2,2,3,3,4,4,4-heptafluoro-n-methylbutan-1-amine Chemical compound CNCC(F)(F)C(F)(F)C(F)(F)F XODUVTJXUOOAKV-UHFFFAOYSA-N 0.000 description 1
- JYWKEVKEKOTYEX-UHFFFAOYSA-N 2,6-dibromo-4-chloroiminocyclohexa-2,5-dien-1-one Chemical compound ClN=C1C=C(Br)C(=O)C(Br)=C1 JYWKEVKEKOTYEX-UHFFFAOYSA-N 0.000 description 1
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- 235000012424 soybean oil Nutrition 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Classifications
-
- 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
-
- 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
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4132182.0 | 1991-09-24 | ||
| DE4132182A DE4132182A1 (de) | 1991-09-24 | 1991-09-24 | 11(beta)-substituierte 14, 17-ethanoestratriene, verfahren zur herstellung dieser verbindungen, sowie ihre verwendung zur herstellung von arzneimitteln |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2119780A1 true CA2119780A1 (en) | 1993-04-01 |
Family
ID=6441613
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002119780A Abandoned CA2119780A1 (en) | 1991-09-24 | 1992-09-24 | 11.beta.-substituted 14,17-ethanoestratrienes, process for preparing these compounds and their use for preparing medicaments |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5502046A (enExample) |
| EP (2) | EP0642529B1 (enExample) |
| JP (1) | JPH07501792A (enExample) |
| AT (1) | ATE146185T1 (enExample) |
| CA (1) | CA2119780A1 (enExample) |
| DE (2) | DE4132182A1 (enExample) |
| DK (1) | DK0642529T3 (enExample) |
| ES (1) | ES2097924T3 (enExample) |
| GR (1) | GR3022692T3 (enExample) |
| WO (1) | WO1993006124A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19724187A1 (de) * | 1997-06-02 | 1998-12-03 | Schering Ag | 11beta-Arylsubstituierte 14,17-Ethanoestratriene, Verfahren zur Herstellung dieser Verbindungen, sowie ihre Verwendung zur Herstellung von Arzneimitteln |
| HUP9802054A3 (en) * | 1997-10-14 | 2001-02-28 | Bayer Ag | Process for producing 4,4,5,5,5-pentafluor-1-pentanol |
| US6054446A (en) * | 1997-12-24 | 2000-04-25 | Sri International | Anti-estrogenic steroids, and associated pharmaceutical compositions and methods of use |
| US6198497B1 (en) | 1998-06-03 | 2001-03-06 | Hewlett-Packard | Adjustment of a laser diode output power compensator |
| EP1131336B1 (en) * | 1998-11-20 | 2002-08-28 | Akzo Nobel N.V. | Estrogenic estra-1,3,5(10)-trienes with differential effects on the alpha and beta estrogen receptors, having a linear hydrocarbon chain of from 5-9 carbon atoms in position 11 |
| GB0025221D0 (en) | 2000-10-14 | 2000-11-29 | Astrazeneca Ab | New process |
| GB0123961D0 (en) * | 2001-10-05 | 2001-11-28 | Astrazeneca Ab | Process and intermediates |
| US20040235791A1 (en) * | 2002-01-25 | 2004-11-25 | Gruskin Elliott A. | Scar reduction |
| DE102008061722A1 (de) | 2008-12-12 | 2010-06-17 | Saltigo Gmbh | Verfahren zur Herstellung von Perfluoralkyl- oder Perfluoralkoxyalkanolen |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2377419A1 (fr) * | 1977-01-13 | 1978-08-11 | Roussel Uclaf | Nouveaux derives steroides 11b-substitues 1,3,5 (10) trieniques, leur procede de preparation et leur application comme medicament |
| FR2528434B1 (fr) * | 1982-06-11 | 1985-07-19 | Roussel Uclaf | Nouveaux 19-nor steroides substitues en 11b et eventuellement en 2, leur procede de preparation et leur application comme medicament |
| FR2618783B1 (fr) * | 1987-07-30 | 1991-02-01 | Roussel Uclaf | Nouveaux 17-aryle steroides, leurs procedes et des intermediaires de preparation comme medicaments et les compositions pharmaceutiques les renfermant |
| DE3838779A1 (de) * | 1988-11-11 | 1990-05-17 | Schering Ag | 14(alpha),17(alpha)-ethano-estratriene |
| DE3925507A1 (de) * | 1989-07-28 | 1991-01-31 | Schering Ag | 14,17(alpha)-etheno- und ethanoestratriene, verfahren zur herstellung dieser verbindungen, sowie ihre verwendung zur herstellung von arzneimitteln |
| RU2087479C1 (ru) * | 1989-11-29 | 1997-08-20 | Шеринг Аг | Эстратриены, содержащие мостик |
-
1991
- 1991-09-24 DE DE4132182A patent/DE4132182A1/de not_active Withdrawn
-
1992
- 1992-09-24 DK DK92920370.1T patent/DK0642529T3/da active
- 1992-09-24 JP JP5505804A patent/JPH07501792A/ja active Pending
- 1992-09-24 EP EP92920370A patent/EP0642529B1/de not_active Expired - Lifetime
- 1992-09-24 ES ES92920370T patent/ES2097924T3/es not_active Expired - Lifetime
- 1992-09-24 WO PCT/EP1992/002210 patent/WO1993006124A1/de not_active Ceased
- 1992-09-24 AT AT92920370T patent/ATE146185T1/de not_active IP Right Cessation
- 1992-09-24 US US08/211,173 patent/US5502046A/en not_active Expired - Fee Related
- 1992-09-24 EP EP92203021A patent/EP0546591A2/de active Pending
- 1992-09-24 DE DE59207687T patent/DE59207687D1/de not_active Expired - Lifetime
- 1992-09-24 CA CA002119780A patent/CA2119780A1/en not_active Abandoned
-
1997
- 1997-02-27 GR GR970400373T patent/GR3022692T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATE146185T1 (de) | 1996-12-15 |
| US5502046A (en) | 1996-03-26 |
| DE4132182A1 (de) | 1993-03-25 |
| ES2097924T3 (es) | 1997-04-16 |
| JPH07501792A (ja) | 1995-02-23 |
| EP0546591A3 (enExample) | 1994-03-09 |
| GR3022692T3 (en) | 1997-05-31 |
| EP0642529A1 (de) | 1995-03-15 |
| EP0546591A2 (de) | 1993-06-16 |
| DE59207687D1 (de) | 1997-01-23 |
| DK0642529T3 (da) | 1997-06-02 |
| EP0642529B1 (de) | 1996-12-11 |
| WO1993006124A1 (de) | 1993-04-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |