DD251356B3 - Verfahren zur herstellung von 17alpha-ethinyl-17beta-hydroxy-18-methyl-4,15-estradien-3-on - Google Patents
Verfahren zur herstellung von 17alpha-ethinyl-17beta-hydroxy-18-methyl-4,15-estradien-3-on Download PDFInfo
- Publication number
- DD251356B3 DD251356B3 DD86290057A DD29005786A DD251356B3 DD 251356 B3 DD251356 B3 DD 251356B3 DD 86290057 A DD86290057 A DD 86290057A DD 29005786 A DD29005786 A DD 29005786A DD 251356 B3 DD251356 B3 DD 251356B3
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- methyl
- estradien
- carbon
- ketone
- hydroxy
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 12
- SIGSPDASOTUPFS-XUDSTZEESA-N gestodene Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](CC)([C@](C=C4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 SIGSPDASOTUPFS-XUDSTZEESA-N 0.000 claims description 9
- ARNWQMJQALNBBV-UHFFFAOYSA-N lithium carbide Chemical compound [Li+].[Li+].[C-]#[C-] ARNWQMJQALNBBV-UHFFFAOYSA-N 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 229960005352 gestodene Drugs 0.000 claims description 7
- 238000003776 cleavage reaction Methods 0.000 claims description 6
- 230000007017 scission Effects 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 4
- 230000008030 elimination Effects 0.000 claims description 2
- 238000003379 elimination reaction Methods 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims 1
- 239000003433 contraceptive agent Substances 0.000 claims 1
- 230000002254 contraceptive effect Effects 0.000 claims 1
- 125000000468 ketone group Chemical group 0.000 claims 1
- 230000003389 potentiating effect Effects 0.000 claims 1
- 239000000583 progesterone congener Substances 0.000 claims 1
- 230000002363 herbicidal effect Effects 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O OSVMTWJCGUFAOD-KZQROQTASA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
- 239000012043 crude product Substances 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- 229910052786 argon Inorganic materials 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- -1 ethylenedioxy Chemical group 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- CURPQRJHLMVQHU-TZTJZIIHSA-N [(8r,9s,10r,13s,14s,15s)-13-ethyl-3,17-dioxo-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-15-yl] 2,2-dimethylpropanoate Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](CC)(C(C[C@@H]4OC(=O)C(C)(C)C)=O)[C@@H]4[C@@H]3CCC2=C1 CURPQRJHLMVQHU-TZTJZIIHSA-N 0.000 description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 3
- 235000006408 oxalic acid Nutrition 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 2
- 150000002084 enol ethers Chemical class 0.000 description 2
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 2
- INJBMNNLSBCVGV-QDWSJHPCSA-N (8r,9r,10s,13r)-13-methyl-2,4,5,6,7,8,9,10,11,12-decahydro-1h-cyclopenta[a]phenanthren-3-one Chemical compound C([C@@H]12)CC(=O)CC1CC[C@@H]1[C@@H]2CC[C@@]2(C)C1=CC=C2 INJBMNNLSBCVGV-QDWSJHPCSA-N 0.000 description 1
- DHBXNPKRAUYBTH-UHFFFAOYSA-N 1,1-ethanedithiol Chemical compound CC(S)S DHBXNPKRAUYBTH-UHFFFAOYSA-N 0.000 description 1
- PGZVFRAEAAXREB-UHFFFAOYSA-N 2,2-dimethylpropanoyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC(=O)C(C)(C)C PGZVFRAEAAXREB-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- MUCRYNWJQNHDJH-OADIDDRXSA-N Ursonic acid Chemical compound C1CC(=O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C MUCRYNWJQNHDJH-OADIDDRXSA-N 0.000 description 1
- JGELGMLHTMVRKQ-VRNBSTIASA-N [(8r,9s,10r,13s,14s,15s)-13-ethyl-3-methoxy-17-oxo-2,7,8,9,10,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-15-yl] 2,2-dimethylpropanoate Chemical compound C1=C(OC)CC[C@@H]2[C@H]3CC[C@](CC)(C(C[C@@H]4OC(=O)C(C)(C)C)=O)[C@@H]4[C@@H]3CC=C21 JGELGMLHTMVRKQ-VRNBSTIASA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000005661 deetherification reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 238000010583 slow cooling Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
Classifications
-
- 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
- C07J1/0051—Estrane derivatives
- C07J1/0059—Estrane derivatives substituted in position 17 by a keto group
-
- 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
- C07J1/0051—Estrane derivatives
- C07J1/0081—Substituted in position 17 alfa and 17 beta
- C07J1/0088—Substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being an unsaturated hydrocarbon group
- C07J1/0096—Alkynyl derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3517466 | 1985-05-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DD251356A5 DD251356A5 (de) | 1987-11-11 |
| DD251356B3 true DD251356B3 (de) | 1993-04-01 |
Family
ID=6270766
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD86290057A DD251356B3 (de) | 1985-05-10 | 1986-05-08 | Verfahren zur herstellung von 17alpha-ethinyl-17beta-hydroxy-18-methyl-4,15-estradien-3-on |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US4719054A (cs) |
| EP (1) | EP0201452B1 (cs) |
| JP (2) | JPH0776231B2 (cs) |
| CN (1) | CN1008820B (cs) |
| AT (1) | ATE45363T1 (cs) |
| AU (1) | AU581138B2 (cs) |
| CA (1) | CA1250570A (cs) |
| CS (1) | CS268817B2 (cs) |
| DD (1) | DD251356B3 (cs) |
| DE (1) | DE3664916D1 (cs) |
| DK (1) | DK171578B1 (cs) |
| ES (1) | ES8704510A1 (cs) |
| GR (1) | GR861126B (cs) |
| HU (2) | HU196430B (cs) |
| IE (1) | IE58798B1 (cs) |
| PT (1) | PT82536B (cs) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3710728A1 (de) * | 1987-03-31 | 1988-10-13 | Schering Ag | Verfahren zur herstellung von 17(alpha)-ethinyl-17ss-hydroxy-18-methyl-4,15-estradien-3-on und die neuen zwischenprodukte fuer dieses verfahren |
| FR2647452A1 (fr) * | 1989-05-24 | 1990-11-30 | Theramex | Nouveaux 19-nor steroides 6-methyles leurs procedes d'obtention, les compositions pharmaceutiques en renfermant et leur conversion en 19-nor pregnadienes 17-substitues |
| IT1271004B (it) * | 1994-09-09 | 1997-05-26 | Ind Chimica Srl | Processo per la preparazione del gestodene |
| EP2354150A1 (en) | 2010-02-09 | 2011-08-10 | Laboratoire Theramex | Process for the preparation of gestodene |
| JP2014505721A (ja) * | 2011-02-17 | 2014-03-06 | ルピン・リミテッド | レボノルゲストレルを調製するための改良された方法 |
| CN103319558B (zh) * | 2012-03-22 | 2016-01-20 | 华润紫竹药业有限公司 | 甾体化合物及其制备方法和用途 |
| CN119751531A (zh) * | 2024-12-26 | 2025-04-04 | 浙江仙琚制药股份有限公司 | 一种左旋乙基甾烯二酮的制备方法 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3214448A (en) * | 1962-07-27 | 1965-10-26 | American Cyanamid Co | 14alpha-hydroxyestrone and ester thereof |
| BE794517A (fr) * | 1972-01-27 | 1973-07-25 | Ishihara Mining & Chemical Co | Herbicide pour l'agriculture |
| DE2223894C3 (de) * | 1972-05-17 | 1981-07-23 | Hoechst Ag, 6000 Frankfurt | Herbizide Mittel auf Basis von Phenoxycarbonsäurederivaten |
| DE2433067B2 (de) * | 1974-07-10 | 1977-11-24 | a- [4-(4" Trifluormethylphenoxy)-phenoxy] -propionsäuren und deren Derivate, Verfahren zu ihrer Herstellung und diese enthaltende herbizide Mittel Hoechst AG, 6000 Frankfurt | Alpha- eckige klammer auf 4-(4' trifluormethylphenoxy)-phenoxy eckige klammer zu -propionsaeuren und deren derivate, verfahren zu ihrer herstellung und diese enthaltende herbizide mittel |
| CS185694B2 (en) * | 1974-07-17 | 1978-10-31 | Ishihara Sangyo Kaisha | Herbicidal agent |
| DE2456068A1 (de) * | 1974-11-23 | 1976-08-12 | Schering Ag | Verfahren zur herstellung von oestren3,17-dion-derivaten |
| GB1560416A (en) * | 1975-09-03 | 1980-02-06 | Rohm & Haas | Trifluoromethylphenyl derivatives |
| DE2546062A1 (de) * | 1975-10-10 | 1977-04-21 | Schering Ag | Delta hoch 15 -steroide |
| US4081537A (en) * | 1975-10-10 | 1978-03-28 | Schering Aktiengesellschaft | Δ15 -Steroids and pharmaceutical compositions thereof |
| DE2601548C2 (de) * | 1976-01-16 | 1984-01-26 | Hoechst Ag, 6230 Frankfurt | 2-[4-(2'-Chlor-4'-bromphenoxy)-phenoxy]-propionsäure und Derivate sowie diese enthaltende herbizide Mittel |
| DE2617804C2 (de) * | 1976-04-23 | 1985-01-24 | Hoechst Ag, 6230 Frankfurt | 2-(4-Phenoxy phenoxy)-propionsäurederivate und ihre Verwendung als Herbizide |
| DE2749104C2 (de) * | 1977-10-31 | 1982-03-25 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Verfahren zur Herstellung von δ↑15↑ -Steroiden |
| US4375981A (en) * | 1979-05-14 | 1983-03-08 | Ppg Industries, Inc. | Method for controlling weed growth using herbicidally 5-(2-chloro-4-trifluoromethyl)-, or (4-trifluoromethyl or 2,6-dichloro-4-trifluoromethylphenoxy)-2-nitro-substituted carbonyl oxime-O-alkyl ethers |
| US4388472A (en) * | 1979-07-18 | 1983-06-14 | Imperial Chemical Industries Plc | Substituted diphenyl ethers |
| EP0023392B1 (en) * | 1979-07-18 | 1984-06-06 | Imperial Chemical Industries Plc | Diphenyl ether compounds, and herbicidal compositions and processes utilising them |
| US4353736A (en) * | 1980-01-17 | 1982-10-12 | Ciba-Geigy Corporation | Method of selectively controlling weeds and herbicidal diphenyl ether oxime derivatives |
| EP0034402B1 (en) * | 1980-02-05 | 1984-08-29 | Imperial Chemical Industries Plc | Method of preparing fluorine-substituted diphenyl ether derivatives and fluorine-substituted halogeno benzene derivatives for use therein |
| US4402727A (en) * | 1981-06-04 | 1983-09-06 | Bayer Aktiengesellschaft | Substituted azolylalkyl phenoxyphenoxyalkane-carboxylates as herbicides and plant growth regulators |
| DE3122174A1 (de) * | 1981-06-04 | 1982-12-30 | Bayer Ag, 5090 Leverkusen | Substituierte phenoxyphenyl-azolylalkylether, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide und pflanzenwuchsregulatoren |
-
1986
- 1986-04-14 CN CN86102560A patent/CN1008820B/zh not_active Expired
- 1986-04-29 GR GR861126A patent/GR861126B/el unknown
- 1986-04-30 DK DK197586A patent/DK171578B1/da active Protection Beyond IP Right Term
- 1986-05-06 CS CS863264A patent/CS268817B2/cs not_active IP Right Cessation
- 1986-05-06 AU AU57155/86A patent/AU581138B2/en not_active Expired
- 1986-05-07 EP EP86730074A patent/EP0201452B1/de not_active Expired
- 1986-05-07 AT AT86730074T patent/ATE45363T1/de not_active IP Right Cessation
- 1986-05-07 ES ES554711A patent/ES8704510A1/es not_active Expired
- 1986-05-07 DE DE8686730074T patent/DE3664916D1/de not_active Expired
- 1986-05-08 PT PT82536A patent/PT82536B/pt unknown
- 1986-05-08 DD DD86290057A patent/DD251356B3/de not_active IP Right Cessation
- 1986-05-09 US US06/861,775 patent/US4719054A/en not_active Expired - Lifetime
- 1986-05-09 IE IE123386A patent/IE58798B1/en not_active IP Right Cessation
- 1986-05-09 HU HU861931A patent/HU196430B/hu unknown
- 1986-05-09 HU HU884022A patent/HU197755B/hu unknown
- 1986-05-09 JP JP61105062A patent/JPH0776231B2/ja not_active Expired - Lifetime
- 1986-05-09 US US06/861,776 patent/US4751329A/en not_active Expired - Fee Related
- 1986-05-09 CA CA000508822A patent/CA1250570A/en not_active Expired
-
1995
- 1995-02-20 JP JP7031190A patent/JP2509467B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| AU581138B2 (en) | 1989-02-09 |
| ATE45363T1 (de) | 1989-08-15 |
| JP2509467B2 (ja) | 1996-06-19 |
| IE861233L (en) | 1986-11-10 |
| PT82536B (pt) | 1988-07-01 |
| AU5715586A (en) | 1986-11-13 |
| ES8704510A1 (es) | 1987-04-16 |
| EP0201452B1 (de) | 1989-08-09 |
| EP0201452A2 (de) | 1986-11-12 |
| JPH0776231B2 (ja) | 1995-08-16 |
| US4751329A (en) | 1988-06-14 |
| CA1250570A (en) | 1989-02-28 |
| CS326486A2 (en) | 1989-08-14 |
| PT82536A (de) | 1986-06-01 |
| ES554711A0 (es) | 1987-04-16 |
| IE58798B1 (en) | 1993-11-17 |
| HU196430B (en) | 1988-11-28 |
| DK197586D0 (da) | 1986-04-30 |
| HU197755B (en) | 1989-05-29 |
| DK197586A (da) | 1986-11-11 |
| US4719054A (en) | 1988-01-12 |
| DE3664916D1 (en) | 1989-09-14 |
| DK171578B1 (da) | 1997-01-27 |
| EP0201452A3 (en) | 1987-07-01 |
| CS268817B2 (en) | 1990-04-11 |
| CN1008820B (zh) | 1990-07-18 |
| JPH07316184A (ja) | 1995-12-05 |
| HUT40679A (en) | 1987-01-28 |
| GR861126B (en) | 1986-09-30 |
| CN86102560A (zh) | 1987-01-21 |
| DD251356A5 (de) | 1987-11-11 |
| JPS61260096A (ja) | 1986-11-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B3 | Exclusive patent (sect. 18(1)) | ||
| ENJ | Ceased due to non-payment of renewal fee |