DE3490728C2 - Androstan-Derivate - Google Patents
Androstan-DerivateInfo
- Publication number
- DE3490728C2 DE3490728C2 DE19843490728 DE3490728A DE3490728C2 DE 3490728 C2 DE3490728 C2 DE 3490728C2 DE 19843490728 DE19843490728 DE 19843490728 DE 3490728 A DE3490728 A DE 3490728A DE 3490728 C2 DE3490728 C2 DE 3490728C2
- Authority
- DE
- Germany
- Prior art keywords
- tumors
- chloroethyl
- tumor
- effect
- hormone
- 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.)
- Expired
Links
- 150000001440 androstane derivatives Chemical class 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 description 31
- 206010028980 Neoplasm Diseases 0.000 description 27
- 230000000259 anti-tumor effect Effects 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 229940088597 hormone Drugs 0.000 description 17
- 239000005556 hormone Substances 0.000 description 17
- 150000003431 steroids Chemical class 0.000 description 17
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 16
- 150000001441 androstanes Chemical class 0.000 description 16
- 241000700159 Rattus Species 0.000 description 15
- 210000001519 tissue Anatomy 0.000 description 15
- NVKAWKQGWWIWPM-ABEVXSGRSA-N 17-β-hydroxy-5-α-Androstan-3-one Chemical compound C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@H]21 NVKAWKQGWWIWPM-ABEVXSGRSA-N 0.000 description 14
- UQFHJDVUQSAVOQ-UHFFFAOYSA-N (2-aminophenyl) acetate Chemical compound CC(=O)OC1=CC=CC=C1N UQFHJDVUQSAVOQ-UHFFFAOYSA-N 0.000 description 13
- 241001465754 Metazoa Species 0.000 description 12
- 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 11
- 239000000824 cytostatic agent Substances 0.000 description 11
- 230000001085 cytostatic effect Effects 0.000 description 11
- 230000003054 hormonal effect Effects 0.000 description 10
- 241000699670 Mus sp. Species 0.000 description 9
- 230000001548 androgenic effect Effects 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 230000002152 alkylating effect Effects 0.000 description 8
- 229960003473 androstanolone Drugs 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 230000001195 anabolic effect Effects 0.000 description 6
- 210000005075 mammary gland Anatomy 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 230000002269 spontaneous effect Effects 0.000 description 6
- 206010061535 Ovarian neoplasm Diseases 0.000 description 5
- 239000003098 androgen Substances 0.000 description 5
- 210000002307 prostate Anatomy 0.000 description 5
- 230000009870 specific binding Effects 0.000 description 5
- 230000004083 survival effect Effects 0.000 description 5
- 231100000331 toxic Toxicity 0.000 description 5
- 230000002588 toxic effect Effects 0.000 description 5
- RQAFMLCWWGDNLI-UHFFFAOYSA-N 2-[4-[bis(2-chloroethyl)amino]phenyl]acetic acid Chemical group OC(=O)CC1=CC=C(N(CCCl)CCCl)C=C1 RQAFMLCWWGDNLI-UHFFFAOYSA-N 0.000 description 4
- QZLYKIGBANMMBK-UGCZWRCOSA-N 5α-Androstane Chemical compound C([C@@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CCC[C@@]2(C)CC1 QZLYKIGBANMMBK-UGCZWRCOSA-N 0.000 description 4
- 206010008342 Cervix carcinoma Diseases 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 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 description 4
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 4
- 201000010881 cervical cancer Diseases 0.000 description 4
- 210000000172 cytosol Anatomy 0.000 description 4
- 229960005309 estradiol Drugs 0.000 description 4
- 230000012010 growth Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 210000000056 organ Anatomy 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- SGDBTWWWUNNDEQ-UHFFFAOYSA-N Merphalan Chemical compound OC(=O)C(N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- FMGSKLZLMKYGDP-USOAJAOKSA-N dehydroepiandrosterone Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 FMGSKLZLMKYGDP-USOAJAOKSA-N 0.000 description 3
- 238000011835 investigation Methods 0.000 description 3
- 230000004060 metabolic process Effects 0.000 description 3
- 210000001672 ovary Anatomy 0.000 description 3
- 108020003175 receptors Proteins 0.000 description 3
- 102000005962 receptors Human genes 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000011287 therapeutic dose Methods 0.000 description 3
- -1 (2-chloroethyl) aminophenylacetic acid ester Chemical class 0.000 description 2
- UIHVAXRVVJJTHU-UHFFFAOYSA-N 2-[bis(2-chloroethyl)amino]acetic acid Chemical group OC(=O)CN(CCCl)CCCl UIHVAXRVVJJTHU-UHFFFAOYSA-N 0.000 description 2
- NLIYXZFSUJHQCB-UHFFFAOYSA-N 2-amino-4-chloro-2-phenylbutanoyl chloride Chemical compound ClCCC(C(=O)Cl)(C1=CC=CC=C1)N NLIYXZFSUJHQCB-UHFFFAOYSA-N 0.000 description 2
- 201000000274 Carcinosarcoma Diseases 0.000 description 2
- FMGSKLZLMKYGDP-UHFFFAOYSA-N Dehydroepiandrosterone Natural products C1C(O)CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CC=C21 FMGSKLZLMKYGDP-UHFFFAOYSA-N 0.000 description 2
- 102000007399 Nuclear hormone receptor Human genes 0.000 description 2
- 108010007568 Protamines Proteins 0.000 description 2
- 102000007327 Protamines Human genes 0.000 description 2
- PDMMFKSKQVNJMI-BLQWBTBKSA-N Testosterone propionate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CC)[C@@]1(C)CC2 PDMMFKSKQVNJMI-BLQWBTBKSA-N 0.000 description 2
- 208000009956 adenocarcinoma Diseases 0.000 description 2
- 230000027455 binding Effects 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 229940124558 contraceptive agent Drugs 0.000 description 2
- 239000003433 contraceptive agent Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940011871 estrogen Drugs 0.000 description 2
- 239000000262 estrogen Substances 0.000 description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 2
- 230000003325 follicular Effects 0.000 description 2
- 231100000508 hormonal effect Toxicity 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 230000002611 ovarian Effects 0.000 description 2
- 229960002847 prasterone Drugs 0.000 description 2
- 229950008679 protamine sulfate Drugs 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229960003604 testosterone Drugs 0.000 description 2
- 229960001712 testosterone propionate Drugs 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 210000004291 uterus Anatomy 0.000 description 2
- VMNRNUNYBVFVQI-QYXZOKGRSA-N (5s,8s,9s,10s,13s,14s)-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one Chemical compound C([C@@H]1CC2)C(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CCC[C@@]2(C)CC1 VMNRNUNYBVFVQI-QYXZOKGRSA-N 0.000 description 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- 206010003694 Atrophy Diseases 0.000 description 1
- 241000219198 Brassica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 108010066551 Cholestenone 5 alpha-Reductase Proteins 0.000 description 1
- 108010077544 Chromatin Proteins 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- 208000006552 Lewis Lung Carcinoma Diseases 0.000 description 1
- 206010025327 Lymphopenia Diseases 0.000 description 1
- BKAYIFDRRZZKNF-VIFPVBQESA-N N-acetylcarnosine Chemical compound CC(=O)NCCC(=O)N[C@H](C(O)=O)CC1=CN=CN1 BKAYIFDRRZZKNF-VIFPVBQESA-N 0.000 description 1
- 206010029350 Neurotoxicity Diseases 0.000 description 1
- 108020005497 Nuclear hormone receptor Proteins 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 206010044221 Toxic encephalopathy Diseases 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 description 1
- 230000003388 anti-hormonal effect Effects 0.000 description 1
- 230000037444 atrophy 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
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 244000144987 brood Species 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 210000003483 chromatin Anatomy 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 230000002254 contraceptive effect Effects 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 108091007930 cytoplasmic receptors Proteins 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000000763 evoking effect Effects 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 108091008039 hormone receptors Proteins 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 230000006651 lactation Effects 0.000 description 1
- 238000002350 laparotomy Methods 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 231100001023 lymphopenia Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 230000007135 neurotoxicity Effects 0.000 description 1
- 231100000228 neurotoxicity Toxicity 0.000 description 1
- 108020004017 nuclear receptors Proteins 0.000 description 1
- 210000004940 nucleus Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 208000025661 ovarian cyst Diseases 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 229950004157 sarcolysin Drugs 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 210000001625 seminal vesicle Anatomy 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 108010068815 steroid hormone 7-alpha-hydroxylase Proteins 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000007847 structural defect Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- 150000003515 testosterones Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 201000010653 vesiculitis Diseases 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0038—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 with an androstane skeleton, including 18- or 19-substituted derivatives, 18-nor derivatives and also derivatives where position 17-beta is substituted by a carbon atom not directly bonded to a further carbon atom and not being part of an amide group
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/SU1984/000033 WO1986000311A1 (fr) | 1984-06-27 | 1984-06-27 | Derives de steroides de series d'androstane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3490728C2 true DE3490728C2 (de) | 1989-09-14 |
Family
ID=21616852
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19843490728 Expired DE3490728C2 (de) | 1984-06-27 | 1984-06-27 | Androstan-Derivate |
| DE19843490728 Pending DE3490728T1 (de) | 1984-06-27 | 1984-06-27 | Steroidderivate der Androstanreihe |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19843490728 Pending DE3490728T1 (de) | 1984-06-27 | 1984-06-27 | Steroidderivate der Androstanreihe |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS61502256A (enExample) |
| CH (1) | CH666276A5 (enExample) |
| DE (2) | DE3490728C2 (enExample) |
| FI (1) | FI84834C (enExample) |
| GB (1) | GB2169900B (enExample) |
| SE (1) | SE457535B (enExample) |
| WO (1) | WO1986000311A1 (enExample) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2702509A1 (de) * | 1976-01-22 | 1977-07-28 | Leo Ab | 17alpha-ester von gestagenen mit antitumor-wirksamkeit, deren herstellung und diese ester enthaltende mittel |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5810393B2 (ja) * | 1978-08-14 | 1983-02-25 | 呉羽化学工業株式会社 | 新規なエストラジオ−ル結合体とその製造方法及び抗腫瘍剤 |
-
1984
- 1984-06-27 CH CH571/86A patent/CH666276A5/de not_active IP Right Cessation
- 1984-06-27 DE DE19843490728 patent/DE3490728C2/de not_active Expired
- 1984-06-27 WO PCT/SU1984/000033 patent/WO1986000311A1/ru not_active Ceased
- 1984-06-27 DE DE19843490728 patent/DE3490728T1/de active Pending
- 1984-06-27 JP JP60500685A patent/JPS61502256A/ja active Granted
- 1984-06-27 GB GB08602936A patent/GB2169900B/en not_active Expired
-
1986
- 1986-02-24 SE SE8600828A patent/SE457535B/sv not_active IP Right Cessation
- 1986-02-25 FI FI860815A patent/FI84834C/fi not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2702509A1 (de) * | 1976-01-22 | 1977-07-28 | Leo Ab | 17alpha-ester von gestagenen mit antitumor-wirksamkeit, deren herstellung und diese ester enthaltende mittel |
Non-Patent Citations (3)
| Title |
|---|
| Chem.Abstr. Vol.101, Nr.7602K (1984) * |
| J.Med.Chem.12, S. 810-818 (1969) * |
| J.Med.Chem.15, S.1158-61 (1972) * |
Also Published As
| Publication number | Publication date |
|---|---|
| FI860815A0 (fi) | 1986-02-25 |
| GB8602936D0 (en) | 1986-03-12 |
| FI84834C (fi) | 1992-01-27 |
| FI84834B (fi) | 1991-10-15 |
| DE3490728T1 (de) | 1986-06-05 |
| SE8600828D0 (sv) | 1986-02-24 |
| WO1986000311A1 (fr) | 1986-01-16 |
| JPH0240079B2 (enExample) | 1990-09-10 |
| GB2169900A (en) | 1986-07-23 |
| SE8600828L (sv) | 1986-02-24 |
| FI860815L (fi) | 1986-02-25 |
| JPS61502256A (ja) | 1986-10-09 |
| GB2169900B (en) | 1988-02-17 |
| SE457535B (sv) | 1989-01-09 |
| CH666276A5 (de) | 1988-07-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3887151T2 (de) | Inhibitoren für zellenzuwachs und methoden für krebsbehandlung. | |
| DE3873870T2 (de) | Androstan-17-carbonsaeureester, verfahren zu ihrer herstellung und arzneimittel, die sie enthalten. | |
| DE2643936A1 (de) | Arzneimittel mit erythropoietischer wirksamkeit | |
| DE3336292C2 (enExample) | ||
| DE2501091A1 (de) | 17-alpha-aethinyl-(5-alpha)-2-androsten-17-beta-ol und sein 17-beta-acetat, verfahren zu ihrer herstellung und ihre therapeutische verwendung | |
| CH621560A5 (en) | Process for the preparation of 3-ketosteroids disubstituted in position 16 | |
| CA1069437A (en) | Steroidal erythropoietic agents and therapeutic compositions and methods | |
| DE2147391B2 (de) | Verfahren zur Herstellung von 13- Äthyl-17 a -äthinyl-17 ß -hydroxy- 16 a methylgona-4-en-3-on | |
| AT395587B (de) | Herstellung und verwendung neuer azolderivate, und sie enthaltende pharmazeutische praeparate | |
| CH666276A5 (de) | Steroidderivate der androstanreihe. | |
| DE60026608T2 (de) | 3-methylen steroid derivate zur behandlung von autoimmunerkrankungen | |
| Sklow | Prolongation of sex hormone effects by adsorption on powdered carbon | |
| DE1620200C3 (de) | 7-Oxo-desacetamido-colchicinderivate, ein Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel. Ausscheidung aus: 1235322 | |
| SE448166B (sv) | Derivat av 11-desoxi-17alfa-hydroxikortikosteron | |
| DE1160852B (de) | Verfahren zur Herstellung von 17 alpha-Chloräthinylsteroiden | |
| DE2109305B2 (de) | 20-Hydroxylierte 17 a - MethyI-19-nor-pregna-4,9diene, Verfahren zu deren Herstellung sowie Zwischenprodukte | |
| DE1926043C3 (de) | Neue Östrogenäther und Verfahren zu ihrer Herstellung | |
| DE2257360C2 (de) | 1-(2-Chloräthyl)-1-nitroso-3-[(2-methyl-4-amino-pyrimidin-5-yl)methyl]harnstoff und Verfahren zu seiner Herstellung | |
| DE2100319B2 (de) | Neue Östranverbindungen, ihre Herstellung und sie enthaltende Arzneimittel | |
| DE3144049A1 (de) | 16(beta)-methyl-8(alpha)-oestradiole, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate | |
| AT216687B (de) | Verfahren zur Herstellung von Testosteronderivaten | |
| DE1620102C3 (de) | 3-Oxime der Androsten- und Gonenreihe, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Mittel | |
| DE2107579C3 (de) | Neue Steroide, Verfahren zu deren Herstellung und diese enthaltendes Mittel | |
| AT208526B (de) | Verfahren zur Herstellung von neuen Estern des Testosterons und 19-Nortestosterons | |
| DE2441647A1 (de) | 17beta-aethinyl-3,17alpha-oestradiolverbindungen, verfahren zu ihrer herstellung, arzneimittel und 17beta-aethinyl-16alpha, 17alpha-epoxyoestran-3-olverbindungen |