DE2409648A1 - Testosteron-3-oxim-derivate, verfahren zu ihrer herstellung und ihre verwendung als verhuetungsmittel post coitum - Google Patents
Testosteron-3-oxim-derivate, verfahren zu ihrer herstellung und ihre verwendung als verhuetungsmittel post coitumInfo
- Publication number
- DE2409648A1 DE2409648A1 DE19742409648 DE2409648A DE2409648A1 DE 2409648 A1 DE2409648 A1 DE 2409648A1 DE 19742409648 DE19742409648 DE 19742409648 DE 2409648 A DE2409648 A DE 2409648A DE 2409648 A1 DE2409648 A1 DE 2409648A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- hydrogen atom
- radical
- general formula
- compound
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 9
- CCDNGLFWWXCDAW-DYKIIFRCSA-N (8r,9s,10r,13s,14s,17s)-3-hydroxyimino-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-ol Chemical class ON=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 CCDNGLFWWXCDAW-DYKIIFRCSA-N 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 46
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- -1 carboxylic acid compound Chemical class 0.000 claims description 11
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 8
- 238000001953 recrystallisation Methods 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000003433 contraceptive agent Substances 0.000 claims description 6
- 238000004587 chromatography analysis Methods 0.000 claims description 5
- 150000002443 hydroxylamines Chemical class 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 229940124558 contraceptive agent Drugs 0.000 claims description 3
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 3
- 150000003515 testosterones Chemical class 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 150000002923 oximes Chemical class 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 230000002254 contraceptive effect Effects 0.000 description 7
- CHNXZKVNWQUJIB-CEGNMAFCSA-N ethisterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 CHNXZKVNWQUJIB-CEGNMAFCSA-N 0.000 description 7
- 229960000445 ethisterone Drugs 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- RRUDCFGSUDOHDG-UHFFFAOYSA-N acetohydroxamic acid Chemical compound CC(O)=NO RRUDCFGSUDOHDG-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000002513 implantation Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical class C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- NYBWUHOMYZZKOR-UHFFFAOYSA-N tes-adt Chemical class C1=C2C(C#C[Si](CC)(CC)CC)=C(C=C3C(SC=C3)=C3)C3=C(C#C[Si](CC)(CC)CC)C2=CC2=C1SC=C2 NYBWUHOMYZZKOR-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 2
- 238000003780 insertion Methods 0.000 description 2
- 230000037431 insertion Effects 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000035935 pregnancy Effects 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- 210000004291 uterus Anatomy 0.000 description 2
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000002513 anti-ovulatory effect Effects 0.000 description 1
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 210000002459 blastocyst Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 1
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- 229940011871 estrogen Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010871 livestock manure Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 229940115165 morning after pill Drugs 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- KBYLNXKSGMLDDM-UHFFFAOYSA-N o-cyclopentylhydroxylamine;hydrochloride Chemical compound Cl.NOC1CCCC1 KBYLNXKSGMLDDM-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003539 oral contraceptive agent Substances 0.000 description 1
- 210000003101 oviduct Anatomy 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000003408 postcoitus contraceptive agent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000026234 pro-estrus Effects 0.000 description 1
- 229960003387 progesterone Drugs 0.000 description 1
- 239000000186 progesterone Substances 0.000 description 1
- 239000000583 progesterone congener Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 230000001150 spermicidal effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 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
- C07J1/0003—Androstane derivatives
- C07J1/0033—Androstane derivatives substituted in position 17 alfa and 17 beta
- C07J1/004—Androstane derivatives substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being an unsaturated hydrocarbon group
- C07J1/0048—Alkynyl derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring the nitrogen atom being directly linked to the cyclopenta(a)hydro phenanthrene skeleton
- C07J41/0016—Oximes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33723673A | 1973-03-01 | 1973-03-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2409648A1 true DE2409648A1 (de) | 1974-09-12 |
Family
ID=23319690
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742409648 Withdrawn DE2409648A1 (de) | 1973-03-01 | 1974-02-28 | Testosteron-3-oxim-derivate, verfahren zu ihrer herstellung und ihre verwendung als verhuetungsmittel post coitum |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5926640B2 (cg-RX-API-DMAC7.html) |
| AT (1) | AT343292B (cg-RX-API-DMAC7.html) |
| CA (1) | CA1034942A (cg-RX-API-DMAC7.html) |
| CH (1) | CH606108A5 (cg-RX-API-DMAC7.html) |
| DE (1) | DE2409648A1 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2219783B1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1452179A (cg-RX-API-DMAC7.html) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2664895B1 (fr) * | 1990-07-20 | 1992-10-30 | Theramex Laboratoire | Nouveaux derives de la 6-methyl 19-nor progesterone, substitues en 3 et leur procede d'obtention. |
| AU3257993A (en) * | 1991-12-22 | 1993-07-28 | Schering Aktiengesellschaft | 3-methylsulphonylhydrazono and 3-oxyimino steroids, a method of preparing them, pharmaceutical preparations containing them and their use in the preparation of drugs |
| JPH0568898U (ja) * | 1992-02-19 | 1993-09-17 | 株式会社明和スクリーン | プルトップ部オープナ |
| HUP0301981A2 (hu) * | 2003-06-30 | 2005-04-28 | Richter Gedeon Vegyészeti Gyár Rt. | Tiszta d-(17alfa)-13-etil-17-hidroxi-18,19-dinor-pregn-4-én-20-in-3-on-3E- és 3Z-oxim izomerek, valamint eljárás az izomer keverékek és a tiszta izomerek előállítására |
| US7816546B2 (en) | 2003-06-30 | 2010-10-19 | Richter Gedeon Vegyeszeti Gyar Rt. | Process for the synthesis of high purity d-(17α)-13-ethyl-17-hydroxy-18,19-dinorpregn-4-ene-20-yn-3-one-oxime |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3299107A (en) * | 1965-02-12 | 1967-01-17 | Searle & Co | 17-(unsaturated hydrocarbon-substituted)-3-hydroxyimino-5alpha-androstan-17beta-ols,alkyl and acyl derivatives thereof |
| US3686237A (en) * | 1969-12-04 | 1972-08-22 | Ortho Pharma Corp | O-(nitroaryl)oximes of 3-keto steroids |
-
1974
- 1974-02-28 DE DE19742409648 patent/DE2409648A1/de not_active Withdrawn
- 1974-02-28 FR FR7406871A patent/FR2219783B1/fr not_active Expired
- 1974-02-28 CA CA193,688A patent/CA1034942A/en not_active Expired
- 1974-02-28 GB GB916974A patent/GB1452179A/en not_active Expired
- 1974-02-28 AT AT165374A patent/AT343292B/de not_active IP Right Cessation
- 1974-03-01 CH CH294474A patent/CH606108A5/xx not_active IP Right Cessation
- 1974-03-01 JP JP49023481A patent/JPS5926640B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5926640B2 (ja) | 1984-06-29 |
| FR2219783A1 (cg-RX-API-DMAC7.html) | 1974-09-27 |
| AT343292B (de) | 1978-05-26 |
| CA1034942A (en) | 1978-07-18 |
| FR2219783B1 (cg-RX-API-DMAC7.html) | 1977-06-03 |
| JPS5029550A (cg-RX-API-DMAC7.html) | 1975-03-25 |
| CH606108A5 (cg-RX-API-DMAC7.html) | 1978-10-13 |
| GB1452179A (en) | 1976-10-13 |
| ATA165374A (de) | 1977-09-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0648778B1 (de) | Neue 11-Benzaldoximestradien-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE3126732C2 (de) | Steroide und sie enthaltende Arzneimittel | |
| DE3844408C2 (de) | In 17 alpha-Stellung substituierte 17ß-Hydroxy-19-norsteroid-Derivate, deren Herstellungsverfahren, und diese enthaltende pharmazeutische Zusammensetzungen | |
| DE4332284C2 (de) | 11-Benzaldoxim-17beta-methoxy-17alpha-methoxymethyl-estradien-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DD126925B3 (de) | Verfahren zur herstellung von delta hoch 15-steroiden | |
| DE1801750A1 (de) | Von Prostaglandinen abgeleitete Verbindungen und Verfahren zu ihrer Herstellung | |
| DE2409648A1 (de) | Testosteron-3-oxim-derivate, verfahren zu ihrer herstellung und ihre verwendung als verhuetungsmittel post coitum | |
| DE3838779A1 (de) | 14(alpha),17(alpha)-ethano-estratriene | |
| DE2702509A1 (de) | 17alpha-ester von gestagenen mit antitumor-wirksamkeit, deren herstellung und diese ester enthaltende mittel | |
| DE2450036A1 (de) | 7 alpha-methyloestr-4-en-3 alpha, 17 beta-diol und derivate desselben, verfahren zu deren herstellung und dieselben enthaltende pharmazeutische praeparate | |
| DD266801A5 (de) | Verfahren zur herstellung einer oestrogen wirksamen verbindung | |
| DE2711516C2 (de) | 17-Spirosultin-Derivate, Zwischenprodukte und Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Zusammensetzungen | |
| DE69319356T2 (de) | Thiolderivate von Gallensäure | |
| CH505080A (de) | Verfahren zur Herstellung neuer Pregnene | |
| DE1493319B1 (de) | 3 beta-Hydroxy-17 alpha-acetoxy-4-pregnen-20-one | |
| DE60026608T2 (de) | 3-methylen steroid derivate zur behandlung von autoimmunerkrankungen | |
| DE3040200C2 (cg-RX-API-DMAC7.html) | ||
| CH643864A5 (de) | 16,17-pyrazolino- und 16,17-isopyrazolino-1, 4-pregnadien-derivate. | |
| EP0186834B1 (de) | 13alpha-Alkyl-17beta-(3-acyloxy-propyl)-gonane | |
| AT277483B (de) | Verfahren zur herstellung von neuen steroidverbindungen verfahren zur herstellung von neuen steroidverbindungen | |
| DE2348197A1 (de) | Noraethindron-o-alkyloxime | |
| DE3706647A1 (de) | 3-desoxo-10ss-alkynylsteroide, verfahren zu deren herstellung und arzneimittel, welche diese enthalten | |
| DE3144049A1 (de) | 16(beta)-methyl-8(alpha)-oestradiole, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate | |
| AT251772B (de) | Verfahren zur Herstellung eines neuen Äthinylderivates des 8-iso-Östrons | |
| DE1958533C3 (de) | Verfahren zur Herstellung von 17 alpha-Propadienyl-Gruppen enthaltenden Steroiden |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |