NO792162L - Fremgangsmaate til fremstilling av 14,15-metylenderivater fra oestranrekken - Google Patents

Fremgangsmaate til fremstilling av 14,15-metylenderivater fra oestranrekken

Info

Publication number: NO792162L
Authority: NO; Norway
Prior art keywords: methylene; estra; trien; methoxy; ols
Prior art date: 1978-06-28

Application number

NO792162A

Other languages

English (en)

Norwegian (no)

Inventor

Kurt Helmut Herbert Ponsold

Richard Prousa

Johann Michael Oettel

Joachim Johannes Strecke

Herbert Wenzel Anton Hoffmann

Original Assignee

Jenapharm Veb

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.)

1978-06-28

Filing date

1979-06-27

Publication date

1980-01-02

1979-06-27 Application filed by Jenapharm Veb filed Critical Jenapharm Veb

1980-01-02 Publication of NO792162L publication Critical patent/NO792162L/no

Links

238000000034 method Methods 0.000 title claims description 16
238000002360 preparation method Methods 0.000 title claims description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 18
GRXPVLPQNMUNNX-MHJRRCNVSA-N estrane Chemical class C1CC2CCCC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 GRXPVLPQNMUNNX-MHJRRCNVSA-N 0.000 claims description 14
239000000203 mixture Substances 0.000 claims description 14
TVZPLCNGKSPOJA-UHFFFAOYSA-N copper zinc Chemical compound [Cu].[Zn] TVZPLCNGKSPOJA-UHFFFAOYSA-N 0.000 claims description 12
UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 claims description 12
150000001875 compounds Chemical class 0.000 claims description 10
-1 arylaminocarbonyloxy Chemical group 0.000 claims description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
229940117975 chromium trioxide Drugs 0.000 claims description 5
WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 5
GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 claims description 5
150000002170 ethers Chemical class 0.000 claims description 4
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 3
125000005195 alkyl amino carbonyloxy group Chemical group 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
150000002162 estranes Chemical class 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
229910052987 metal hydride Inorganic materials 0.000 claims description 2
150000004681 metal hydrides Chemical class 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
230000002829 reductive effect Effects 0.000 claims description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 25
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 11
230000008018 melting Effects 0.000 description 10
238000002844 melting Methods 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 9
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
230000002349 favourable effect Effects 0.000 description 8
NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 description 7
230000000694 effects Effects 0.000 description 7
238000002513 implantation Methods 0.000 description 7
230000002452 interceptive effect Effects 0.000 description 7
230000035935 pregnancy Effects 0.000 description 7
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
230000005764 inhibitory process Effects 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
235000019270 ammonium chloride Nutrition 0.000 description 5
FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 5
IMSSROKUHAOUJS-MJCUULBUSA-N mestranol Chemical compound C1C[C@]2(C)[C@@](C#C)(O)CC[C@H]2[C@@H]2CCC3=CC(OC)=CC=C3[C@H]21 IMSSROKUHAOUJS-MJCUULBUSA-N 0.000 description 5
229960001390 mestranol Drugs 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
239000012279 sodium borohydride Substances 0.000 description 5
229910000033 sodium borohydride Inorganic materials 0.000 description 5
230000001836 utereotrophic effect Effects 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
229910052786 argon Inorganic materials 0.000 description 4
238000010494 dissociation reaction Methods 0.000 description 4
230000005593 dissociations Effects 0.000 description 4
230000001076 estrogenic effect Effects 0.000 description 4
239000012280 lithium aluminium hydride Substances 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
239000002904 solvent Substances 0.000 description 4
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
230000002054 antogonadotrophic effect Effects 0.000 description 3
230000004071 biological effect Effects 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
239000010410 layer Substances 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
ZGPUVZXQCFMRCI-UHFFFAOYSA-N 1,2-dimethoxyethane;ethoxyethane Chemical compound CCOCC.COCCOC ZGPUVZXQCFMRCI-UHFFFAOYSA-N 0.000 description 2
BFPYWIDHMRZLRN-UHFFFAOYSA-N 17alpha-ethynyl estradiol Natural products OC1=CC=C2C3CCC(C)(C(CC4)(O)C#C)C4C3CCC2=C1 BFPYWIDHMRZLRN-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
BFPYWIDHMRZLRN-SLHNCBLASA-N Ethinyl estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 BFPYWIDHMRZLRN-SLHNCBLASA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
230000001833 anti-estrogenic effect Effects 0.000 description 2
230000001838 anti-progestagenic effect Effects 0.000 description 2
WPUJEWVVTKLMQI-UHFFFAOYSA-N benzene;ethoxyethane Chemical compound CCOCC.C1=CC=CC=C1 WPUJEWVVTKLMQI-UHFFFAOYSA-N 0.000 description 2
229960002568 ethinylestradiol Drugs 0.000 description 2
230000035558 fertility Effects 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
239000005457 ice water Substances 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
KWJWXRZFIVSLKX-MLODVTASSA-N sts 593 Chemical compound C([C@@H]1C2=CC=C(C=C2CC[C@H]11)OC)C[C@]2(C)[C@@H](O)C[C@@H]3[C@@]21C3 KWJWXRZFIVSLKX-MLODVTASSA-N 0.000 description 2
239000000725 suspension Substances 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
PYTMYKVIJXPNBD-OQKDUQJOSA-N 2-[4-[(z)-2-chloro-1,2-diphenylethenyl]phenoxy]-n,n-diethylethanamine;hydron;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(/Cl)C1=CC=CC=C1 PYTMYKVIJXPNBD-OQKDUQJOSA-N 0.000 description 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
206010067572 Oestrogenic effect Diseases 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
238000006932 Simmons-Smith cyclopropanation reaction Methods 0.000 description 1
229910001115 Zinc-copper couple Inorganic materials 0.000 description 1
WAHQVRCNDCHDIB-QZYSPNBYSA-N [(3s,8r,9s,10r,13s,14s,17r)-17-acetyl-17-acetyloxy-6,10,13-trimethyl-1,2,3,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-yl] 3-cyclopentylpropanoate Chemical compound O([C@@H]1C=C2C(C)=C[C@H]3[C@@H]4CC[C@]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)(OC(=O)C)C(C)=O)C(=O)CCC1CCCC1 WAHQVRCNDCHDIB-QZYSPNBYSA-N 0.000 description 1
KWJWXRZFIVSLKX-FAQOMCGWSA-N ac1l59vo Chemical compound C([C@@H]1C2=CC=C(C=C2CC[C@H]11)OC)C[C@]2(C)[C@@H](O)C[C@H]3[C@]21C3 KWJWXRZFIVSLKX-FAQOMCGWSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
230000001195 anabolic effect Effects 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000001548 androgenic effect Effects 0.000 description 1
230000002280 anti-androgenic effect Effects 0.000 description 1
230000003388 anti-hormonal effect Effects 0.000 description 1
238000007664 blowing Methods 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
229910002091 carbon monoxide Inorganic materials 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
229940046989 clomiphene citrate Drugs 0.000 description 1
229910000365 copper sulfate Inorganic materials 0.000 description 1
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000002124 endocrine Effects 0.000 description 1
239000000328 estrogen antagonist Substances 0.000 description 1
235000019439 ethyl acetate Nutrition 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
230000003054 hormonal effect Effects 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
239000005556 hormone Substances 0.000 description 1
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
239000007943 implant Substances 0.000 description 1
239000000411 inducer Substances 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
ANAFTYVSHCSQPP-UHFFFAOYSA-N lithium;trimethoxyalumane Chemical compound [Li].CO[Al](OC)OC ANAFTYVSHCSQPP-UHFFFAOYSA-N 0.000 description 1
HTBVGZAVHBZXMS-UHFFFAOYSA-N lithium;tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Li].[Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] HTBVGZAVHBZXMS-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
230000016087 ovulation Effects 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000036961 partial effect Effects 0.000 description 1
230000000757 progestagenic effect Effects 0.000 description 1
239000000583 progesterone congener Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
210000004291 uterus Anatomy 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002023 wood Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 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
- C07J53/004—3 membered carbocyclic rings
- 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
- A61P5/06—Drugs for disorders of the endocrine system of the anterior pituitary hormones, e.g. TSH, ACTH, FSH, LH, PRL, GH
- A61P5/08—Drugs for disorders of the endocrine system of the anterior pituitary hormones, e.g. TSH, ACTH, FSH, LH, PRL, GH for decreasing, blocking or antagonising the activity of the anterior pituitary hormones
- 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

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
Endocrinology (AREA)
Diabetes (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Photoreceptors In Electrophotography (AREA)
Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

NO792162A 1978-06-28 1979-06-27 Fremgangsmaate til fremstilling av 14,15-metylenderivater fra oestranrekken NO792162L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DD20632378A DD145919B1 (de)	1978-06-28	1978-06-28	Verfahren zur herstellung von 14,1 -methylenderivaten der oestranreihe

Publications (1)

Publication Number	Publication Date
NO792162L true NO792162L (no)	1980-01-02

Family

ID=5513311

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO792162A NO792162L (no)	1978-06-28	1979-06-27	Fremgangsmaate til fremstilling av 14,15-metylenderivater fra oestranrekken

Country Status (20)

Country	Link
US (1)	US4231946A (xx)
JP (1)	JPS559071A (xx)
BE (1)	BE877197A (xx)
BR (1)	BR7903124A (xx)
CA (1)	CA1134346A (xx)
CS (1)	CS208981B1 (xx)
DD (1)	DD145919B1 (xx)
DE (1)	DE2911612A1 (xx)
DK (1)	DK260579A (xx)
ES (1)	ES481985A1 (xx)
FI (1)	FI792032A (xx)
FR (1)	FR2429797B1 (xx)
GB (1)	GB2027030B (xx)
HU (1)	HU180482B (xx)
IT (1)	IT1164106B (xx)
NL (1)	NL7905020A (xx)
NO (1)	NO792162L (xx)
SE (1)	SE7905658L (xx)
SU (1)	SU1087525A1 (xx)
YU (1)	YU147479A (xx)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE4102244A1 (de) *	1991-01-24	1992-07-30	Schering Ag	14,16ss-ethano-15ss, 16(pfeil hoch)1(pfeil hoch)-cyclo-14ss-estra-1,3,5(10)-triene
DE4239946C2 (de) *	1992-11-27	2001-09-13	Jenapharm Gmbh	Estranderivate mit einer 14alpha,15alpha-Methylengruppe und Verfahren zu ihrer Herstellung
DE4239945C2 (de) *	1992-11-27	2002-11-28	Jenapharm Gmbh	14 alpha, 15 alpha-Methylensteroide und Verfahren zu ihrer Herstellung
DE4322186A1 (de) *	1993-07-03	1995-01-12	Jenapharm Gmbh	Oral estrogen wirksame Ester des 14alpha, 15alpha-Methylen-estradiols
DE4326240A1 (de) *	1993-08-02	1995-02-09	Schering Ag	15,15-Dialkyl-substituierte Derivate des Estradiols
DE4338314C1 (de) *	1993-11-10	1995-03-30	Jenapharm Gmbh	Pharmazeutische Präparate zur Prophylaxe und Therapie radikalvermittelter Zellschädigungen
DE4429397C2 (de) *	1994-08-09	2003-11-20	Jenapharm Gmbh	Estra-1,3,5(10)-trien-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Zusammensetzungen
DE4447715C2 (de) *	1994-08-09	1998-02-05	Jenapharm Gmbh	Verwendung von Estra-1,3,5(10)-trien-Derivaten zur hormonalen Behandlung von Prostatakarzinomen
DE4441462C1 (de) *	1994-11-22	1996-05-23	Jenapharm Gmbh	Verfahren zur stereoselektiven Reduktion von 17-Oxo-Steroiden
DE19537626A1 (de) *	1995-10-10	1997-04-17	Jenapharm Gmbh	Steroide mit einer 14, 15-Methylengruppe
DE19906159A1 (de) *	1999-02-09	2000-08-10	Schering Ag	16-Hydroxyestratriene als selektiv wirksame Estrogene
US6593321B2 (en) *	2001-06-11	2003-07-15	Southwest Foundation For Biomedical Research	2-alkoxyestradiol analogs with antiproliferative and antimitotic activity
US20120225849A1 (en) *	2011-03-01	2012-09-06	The University Of Kansas	2-Methoxyestradiol (2-ME2) Prodrug with Enhanced Bioavailability for Prophylaxis or Treatment of Cancerous or Non-Cancerous Condition
DE102012016476A1 (de)	2012-08-17	2014-02-20	Max Franz	Chirale Azetidincarbonsäure-Derivate

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3232963A (en) *	1963-09-30	1966-02-01	Tufts College	16,16-ethylenetestosterone derivatives
NL125069C (xx) *	1963-12-24
DE1288086B (xx) *	1963-12-26	1969-01-30

1978
- 1978-06-28 DD DD20632378A patent/DD145919B1/de not_active IP Right Cessation
1979
- 1979-03-24 DE DE19792911612 patent/DE2911612A1/de not_active Withdrawn
- 1979-05-21 BR BR7903124A patent/BR7903124A/pt unknown
- 1979-06-14 GB GB7920725A patent/GB2027030B/en not_active Expired
- 1979-06-21 DK DK260579A patent/DK260579A/da not_active Application Discontinuation
- 1979-06-22 BE BE0/195906A patent/BE877197A/xx not_active IP Right Cessation
- 1979-06-22 US US06/050,998 patent/US4231946A/en not_active Expired - Lifetime
- 1979-06-22 YU YU01474/79A patent/YU147479A/xx unknown
- 1979-06-25 IT IT49530/79A patent/IT1164106B/it active
- 1979-06-26 FR FR7916427A patent/FR2429797B1/fr not_active Expired
- 1979-06-27 CS CS794438A patent/CS208981B1/cs unknown
- 1979-06-27 FI FI792032A patent/FI792032A/fi not_active Application Discontinuation
- 1979-06-27 SU SU792781813A patent/SU1087525A1/ru active
- 1979-06-27 SE SE7905658A patent/SE7905658L/xx not_active Application Discontinuation
- 1979-06-27 CA CA000330690A patent/CA1134346A/en not_active Expired
- 1979-06-27 ES ES481985A patent/ES481985A1/es not_active Expired
- 1979-06-27 JP JP8124079A patent/JPS559071A/ja active Pending
- 1979-06-27 NL NL7905020A patent/NL7905020A/nl unknown
- 1979-06-27 HU HU79JE878A patent/HU180482B/hu unknown
- 1979-06-27 NO NO792162A patent/NO792162L/no unknown

Also Published As

Publication number	Publication date
NL7905020A (nl)	1980-01-03
DD145919B1 (de)	1982-06-30
GB2027030A (en)	1980-02-13
GB2027030B (en)	1982-09-02
YU147479A (en)	1982-10-31
DE2911612A1 (de)	1980-01-10
SU1087525A1 (ru)	1984-04-23
FR2429797B1 (xx)	1981-02-27
CS208981B1 (en)	1981-10-30
FI792032A (fi)	1979-12-29
DD145919A1 (de)	1981-01-14
DK260579A (da)	1979-12-29
HU180482B (en)	1983-03-28
SE7905658L (sv)	1979-12-29
BE877197A (fr)	1979-10-15
CA1134346A (en)	1982-10-26
ES481985A1 (es)	1980-07-01
JPS559071A (en)	1980-01-22
IT7949530A0 (it)	1979-06-25
BR7903124A (pt)	1981-01-13
FR2429797A1 (xx)	1980-01-25
IT1164106B (it)	1987-04-08
US4231946A (en)	1980-11-04

Publication	Publication Date	Title
NO792162L (no)	1980-01-02	Fremgangsmaate til fremstilling av 14,15-metylenderivater fra oestranrekken
US2705237A (en)	1955-03-29	Process for producing steroid trienes
Nussim et al.	1964	The hydration of unsaturated steroids by the Brown hydroboration reaction. I. Monounsaturated steroids
NZ223924A (en)	1991-12-23	19,11beta-bridged steroids and pharmaceutical compositions
HU191131B (en)	1987-01-28	Process for preparing 13-alpha-alkyl-gonanes and pharmaceutical compositions containing such compounds
CH630392A5 (de)	1982-06-15	Verfahren zur herstellung neuer delta(15)-steroide.
Smith et al.	1964	856. Totally synthetic steroid hormones. Part II. 13β-Alkylgona-1, 3, 5 (10)-trienes, 13β-alkygon-4-en-3-ones, and related compounds
US3413321A (en)	1968-11-26	Selected 17-fluoro-delta16 steroids
US3385871A (en)	1968-05-28	Halogenated cyclopropyl and cyclopropenyl estratrienes and process for their preparation
EP0318490B1 (de)	1992-01-29	14,17-g(b)-ETHANO-14-g(b)-ESTRATRIENE, VERFAHREN ZU DEREN HERSTELLUNG UND DIESE ENTHALTENDE PHARMAZEUTISCHE PRÄPARATE
US3210388A (en)	1965-10-05	13alpha-fluoro-17beta-methyl-18-nor steroids
WO1991001994A1 (de)	1991-02-21	11β-SUBSTITUIERTE 16α,17α-METHYLEN-ESTRA-4,9-DIEN-3-ONE
US3347878A (en)	1967-10-17	Selected 17, 17-difluoro steroids of the estrane series
IE44775B1 (en)	1982-03-24	D-homosteroids
DE3619413C2 (de)	2000-04-06	9alpha, 10alpha-Methylen-Estrene, deren Herstellung und diese enthaltende pharmazeutische Präparate
US3169957A (en)	1965-02-16	Triterpenoid acid derivatives and compounds produced therefrom
US3041359A (en)	1962-06-26	2, 2-dialkyl androgenic type hormones
US3450720A (en)	1969-06-17	3-difluoromethylene steroids
US3467652A (en)	1969-09-16	Synthesis of gonane derivatives
CH374654A (de)	1964-01-31	Verfahren zur Herstellung von Steroidalkyläthern
US2715637A (en)	1955-08-16	Process for producing detla4-3-ketosteroids and intermediates thereof
DE1568175C3 (de)	1977-06-08	17 alpha-Alka-1 ',3-diinylsteroide und Verfahren zu ihrer Herstellung
US3564027A (en)	1971-02-16	Novel 1-methyl-oestrene compounds
Coombs et al.	1975	Synthesis of 9, 11-disubstituted 19-nor-steroids
AT234916B (de)	1964-07-27	Verfahren zur Herstellung von Alkyläthern tertiärer Steroidalkohole