DE1593184B2 - 19-nortesteron-diester von dicarbonsaeuren und verfahren zu deren herstellung - Google Patents
19-nortesteron-diester von dicarbonsaeuren und verfahren zu deren herstellungInfo
- Publication number
- DE1593184B2 DE1593184B2 DE19661593184 DE1593184A DE1593184B2 DE 1593184 B2 DE1593184 B2 DE 1593184B2 DE 19661593184 DE19661593184 DE 19661593184 DE 1593184 A DE1593184 A DE 1593184A DE 1593184 B2 DE1593184 B2 DE 1593184B2
- Authority
- DE
- Germany
- Prior art keywords
- acid
- nortestosterone
- anabolic
- testosterone
- androgenic
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 4
- 239000002253 acid Substances 0.000 title claims 4
- 150000007513 acids Chemical class 0.000 title claims 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- 229960004719 nandrolone Drugs 0.000 claims description 35
- NPAGDVCDWIYMMC-IZPLOLCNSA-N nandrolone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 NPAGDVCDWIYMMC-IZPLOLCNSA-N 0.000 claims description 31
- 230000001195 anabolic effect Effects 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 13
- 230000001548 androgenic effect Effects 0.000 claims description 9
- -1 19-nortestosterone diesters Chemical class 0.000 claims description 7
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 4
- 241000700159 Rattus Species 0.000 claims description 3
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 claims description 3
- IRQUJNVGEAJGSD-WUOGMODZSA-N 4-[[(8r,9s,10r,13s,14s,17s)-13-methyl-3-oxo-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl]oxy]-4-oxobutanoic acid Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@H](CC4)OC(=O)CCC(O)=O)[C@@H]4[C@@H]3CCC2=C1 IRQUJNVGEAJGSD-WUOGMODZSA-N 0.000 claims description 2
- 239000001361 adipic acid Substances 0.000 claims description 2
- 235000011037 adipic acid Nutrition 0.000 claims description 2
- 210000001625 seminal vesicle Anatomy 0.000 claims description 2
- DXNCZXXFRKPEPY-UHFFFAOYSA-N tridecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCC(O)=O DXNCZXXFRKPEPY-UHFFFAOYSA-N 0.000 claims description 2
- 201000010653 vesiculitis Diseases 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 6
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 claims 6
- 150000001991 dicarboxylic acids Chemical class 0.000 claims 5
- 230000002349 favourable effect Effects 0.000 claims 4
- 229960003604 testosterone Drugs 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 230000032050 esterification Effects 0.000 claims 2
- 238000005886 esterification reaction Methods 0.000 claims 2
- 238000002474 experimental method Methods 0.000 claims 2
- 230000000144 pharmacologic effect Effects 0.000 claims 2
- 230000001225 therapeutic effect Effects 0.000 claims 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
- 230000004584 weight gain Effects 0.000 claims 2
- 235000019786 weight gain Nutrition 0.000 claims 2
- KXUGUWTUFUWYRS-UHFFFAOYSA-N 1-methylimidazole-4-sulfonyl chloride Chemical compound CN1C=NC(S(Cl)(=O)=O)=C1 KXUGUWTUFUWYRS-UHFFFAOYSA-N 0.000 claims 1
- FYSGWYBIKGUVJQ-UHFFFAOYSA-N 2,2,3,3-tetramethylhexanedioic acid Chemical compound OC(=O)C(C)(C)C(C)(C)CCC(O)=O FYSGWYBIKGUVJQ-UHFFFAOYSA-N 0.000 claims 1
- ORGPUALGNXTPAW-UHFFFAOYSA-N 2,6-dichloro-n-(1-cyanocycloheptyl)benzamide Chemical compound ClC1=CC=CC(Cl)=C1C(=O)NC1(C#N)CCCCCC1 ORGPUALGNXTPAW-UHFFFAOYSA-N 0.000 claims 1
- WMRCTEPOPAZMMN-UHFFFAOYSA-N 2-undecylpropanedioic acid Chemical compound CCCCCCCCCCCC(C(O)=O)C(O)=O WMRCTEPOPAZMMN-UHFFFAOYSA-N 0.000 claims 1
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 claims 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 1
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 1
- 230000009286 beneficial effect Effects 0.000 claims 1
- 150000001555 benzenes Chemical class 0.000 claims 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 230000015556 catabolic process Effects 0.000 claims 1
- 239000012320 chlorinating reagent Substances 0.000 claims 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 claims 1
- 239000012024 dehydrating agents Substances 0.000 claims 1
- 230000018109 developmental process Effects 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 230000000857 drug effect Effects 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 239000001530 fumaric acid Substances 0.000 claims 1
- 235000013922 glutamic acid Nutrition 0.000 claims 1
- 239000004220 glutamic acid Substances 0.000 claims 1
- 230000014759 maintenance of location Effects 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 239000011976 maleic acid Substances 0.000 claims 1
- 230000000956 myotropic effect Effects 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 235000006408 oxalic acid Nutrition 0.000 claims 1
- 150000003022 phthalic acids Chemical class 0.000 claims 1
- 230000002035 prolonged effect Effects 0.000 claims 1
- 210000002307 prostate Anatomy 0.000 claims 1
- 235000018102 proteins Nutrition 0.000 claims 1
- 102000004169 proteins and genes Human genes 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 230000008929 regeneration Effects 0.000 claims 1
- 238000011069 regeneration method Methods 0.000 claims 1
- 230000035945 sensitivity Effects 0.000 claims 1
- 229960003410 testosterone decanoate Drugs 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- MAZWDMBCPDUFDJ-UHFFFAOYSA-N trans-Traumatinsaeure Natural products OC(=O)CCCCCCCCC=CC(O)=O MAZWDMBCPDUFDJ-UHFFFAOYSA-N 0.000 claims 1
- MAZWDMBCPDUFDJ-VQHVLOKHSA-N traumatic acid Chemical compound OC(=O)CCCCCCCC\C=C\C(O)=O MAZWDMBCPDUFDJ-VQHVLOKHSA-N 0.000 claims 1
- 238000002844 melting Methods 0.000 description 16
- 230000008018 melting Effects 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 description 3
- 230000007774 longterm Effects 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- QQVIHTHCMHWDBS-UHFFFAOYSA-L isophthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC(C([O-])=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-L 0.000 description 1
- 229960001935 nandrolone decanoate Drugs 0.000 description 1
- UBWXUGDQUBIEIZ-QNTYDACNSA-N nandrolone phenpropionate Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@H]4CCC(=O)C=C4CC3)CC[C@@]21C)C(=O)CCC1=CC=CC=C1 UBWXUGDQUBIEIZ-QNTYDACNSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- LWBHHRRTOZQPDM-UHFFFAOYSA-N undecanedioic acid Chemical compound OC(=O)CCCCCCCCCC(O)=O LWBHHRRTOZQPDM-UHFFFAOYSA-N 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL6513946 | 1965-10-28 | ||
| NL656513946A NL147740B (nl) | 1965-10-28 | 1965-10-28 | Werkwijze ter bereiding van dicarbonzuuresters van 19-nor-testosteron met verlengde anabole werking, alsmede gevormd farmaceutisch preparaat. |
| DEN0029410 | 1966-10-26 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1593184A1 DE1593184A1 (de) | 1970-07-30 |
| DE1593184B2 true DE1593184B2 (de) | 1976-01-15 |
| DE1593184C3 DE1593184C3 (en, 2012) | 1976-08-26 |
Family
ID=19794488
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661593184 Granted DE1593184B2 (de) | 1965-10-28 | 1966-10-26 | 19-nortesteron-diester von dicarbonsaeuren und verfahren zu deren herstellung |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3479375A (en, 2012) |
| AT (1) | AT272542B (en, 2012) |
| BE (1) | BE689040A (en, 2012) |
| BR (1) | BR6684141D0 (en, 2012) |
| CH (1) | CH474496A (en, 2012) |
| DE (1) | DE1593184B2 (en, 2012) |
| DK (1) | DK114692B (en, 2012) |
| ES (1) | ES332763A1 (en, 2012) |
| FI (1) | FI45317C (en, 2012) |
| FR (1) | FR1504825A (en, 2012) |
| GB (1) | GB1149256A (en, 2012) |
| IL (1) | IL26690A (en, 2012) |
| NL (1) | NL147740B (en, 2012) |
| SE (1) | SE323072B (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7415669A (nl) * | 1974-12-02 | 1976-06-04 | Akzo Nv | Werkwijze ter bereiding van een nieuwe ester van 19-nor-testosteron. |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB841167A (en) * | 1956-12-10 | 1960-07-13 | Chimiotherapie Lab Franc | Process for the production of a new acylated derivative of 19-nor-testosterone |
| US2999102A (en) * | 1959-10-14 | 1961-09-05 | Thomae Gmbh Dr K | Bis-(steroid-21)-dicarboxylic acid esters |
-
1965
- 1965-10-28 NL NL656513946A patent/NL147740B/xx unknown
-
1966
- 1966-10-14 US US586617A patent/US3479375A/en not_active Expired - Lifetime
- 1966-10-14 IL IL26690A patent/IL26690A/xx unknown
- 1966-10-20 FI FI662763A patent/FI45317C/fi active
- 1966-10-21 GB GB47262/66A patent/GB1149256A/en not_active Expired
- 1966-10-24 CH CH1544366A patent/CH474496A/de not_active IP Right Cessation
- 1966-10-26 ES ES0332763A patent/ES332763A1/es not_active Expired
- 1966-10-26 DE DE19661593184 patent/DE1593184B2/de active Granted
- 1966-10-27 FR FR81742A patent/FR1504825A/fr not_active Expired
- 1966-10-27 SE SE14751/66A patent/SE323072B/xx unknown
- 1966-10-27 BR BR184141/66A patent/BR6684141D0/pt unknown
- 1966-10-28 AT AT1003966A patent/AT272542B/de active
- 1966-10-28 BE BE689040D patent/BE689040A/xx unknown
- 1966-10-28 DK DK563166AA patent/DK114692B/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1149256A (en) | 1969-04-23 |
| SE323072B (en, 2012) | 1970-04-27 |
| FI45317C (fi) | 1972-05-10 |
| BR6684141D0 (pt) | 1973-12-27 |
| IL26690A (en) | 1970-06-17 |
| DK114692B (da) | 1969-07-28 |
| BE689040A (en, 2012) | 1967-04-28 |
| US3479375A (en) | 1969-11-18 |
| FI45317B (en, 2012) | 1972-01-31 |
| AT272542B (de) | 1969-07-10 |
| NL6513946A (en, 2012) | 1967-05-02 |
| ES332763A1 (es) | 1967-07-16 |
| DE1593184A1 (de) | 1970-07-30 |
| CH474496A (de) | 1969-06-30 |
| FR1504825A (fr) | 1967-12-08 |
| NL147740B (nl) | 1975-11-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |