FI84834C - Foerfarande foer framstaellning av terapeutiskt anvaendbara steroidderivat av androstanserien. - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara steroidderivat av androstanserien. Download PDFInfo
- Publication number
- FI84834C FI84834C FI860815A FI860815A FI84834C FI 84834 C FI84834 C FI 84834C FI 860815 A FI860815 A FI 860815A FI 860815 A FI860815 A FI 860815A FI 84834 C FI84834 C FI 84834C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- compound
- color
- compounds
- chloroethyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 113
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 45
- 239000000460 chlorine Substances 0.000 claims description 28
- 150000003431 steroids Chemical class 0.000 claims description 22
- 150000001441 androstanes Chemical class 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 claims description 11
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 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 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 4
- 230000009467 reduction Effects 0.000 claims description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 4
- 239000012279 sodium borohydride Substances 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 239000011630 iodine Substances 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 238000009472 formulation Methods 0.000 claims 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 42
- 206010028980 Neoplasm Diseases 0.000 description 33
- UQFHJDVUQSAVOQ-UHFFFAOYSA-N (2-aminophenyl) acetate Chemical compound CC(=O)OC1=CC=CC=C1N UQFHJDVUQSAVOQ-UHFFFAOYSA-N 0.000 description 30
- 241001465754 Metazoa Species 0.000 description 24
- 230000000259 anti-tumor effect Effects 0.000 description 24
- 230000001548 androgenic effect Effects 0.000 description 20
- 238000011282 treatment Methods 0.000 description 20
- 241000700159 Rattus Species 0.000 description 19
- 229940088597 hormone Drugs 0.000 description 19
- 239000005556 hormone Substances 0.000 description 19
- 210000001519 tissue Anatomy 0.000 description 18
- 230000000694 effects Effects 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 230000001195 anabolic effect Effects 0.000 description 13
- 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 12
- 230000003054 hormonal effect Effects 0.000 description 12
- 241000699670 Mus sp. Species 0.000 description 11
- -1 androstane series steroid Chemical class 0.000 description 11
- 108020003175 receptors Proteins 0.000 description 11
- 102000005962 receptors Human genes 0.000 description 11
- 229960003473 androstanolone Drugs 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 206010061535 Ovarian neoplasm Diseases 0.000 description 9
- 210000002307 prostate Anatomy 0.000 description 9
- 230000009870 specific binding Effects 0.000 description 9
- 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 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 125000000068 chlorophenyl group Chemical group 0.000 description 8
- 230000012010 growth Effects 0.000 description 8
- 239000000126 substance Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 206010006187 Breast cancer Diseases 0.000 description 6
- SGDBTWWWUNNDEQ-UHFFFAOYSA-N Merphalan Chemical compound OC(=O)C(N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-UHFFFAOYSA-N 0.000 description 6
- 230000027455 binding Effects 0.000 description 6
- 238000005886 esterification reaction Methods 0.000 description 6
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- 229950004157 sarcolysin Drugs 0.000 description 6
- 230000004614 tumor growth Effects 0.000 description 6
- 241000219198 Brassica Species 0.000 description 5
- 235000003351 Brassica cretica Nutrition 0.000 description 5
- 235000003343 Brassica rupestris Nutrition 0.000 description 5
- 230000002152 alkylating effect Effects 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 5
- 239000000824 cytostatic agent Substances 0.000 description 5
- 230000001419 dependent effect Effects 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
- 229960005309 estradiol Drugs 0.000 description 5
- 229930182833 estradiol Natural products 0.000 description 5
- 235000010460 mustard Nutrition 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 230000002269 spontaneous effect Effects 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000011287 therapeutic dose Methods 0.000 description 5
- 125000005999 2-bromoethyl group Chemical group 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 210000000172 cytosol Anatomy 0.000 description 4
- 230000001085 cytostatic effect Effects 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 230000002611 ovarian Effects 0.000 description 4
- 230000002265 prevention Effects 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- 231100000419 toxicity Toxicity 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
- UIHVAXRVVJJTHU-UHFFFAOYSA-N 2-[bis(2-chloroethyl)amino]acetic acid Chemical group OC(=O)CN(CCCl)CCCl UIHVAXRVVJJTHU-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 201000009030 Carcinoma Diseases 0.000 description 3
- FMGSKLZLMKYGDP-UHFFFAOYSA-N Dehydroepiandrosterone Natural products C1C(O)CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CC=C21 FMGSKLZLMKYGDP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000001133 acceleration Effects 0.000 description 3
- 239000002168 alkylating agent Substances 0.000 description 3
- 229940100198 alkylating agent Drugs 0.000 description 3
- 239000003098 androgen Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- FMGSKLZLMKYGDP-USOAJAOKSA-N dehydroepiandrosterone Chemical class 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
- 239000003480 eluent Substances 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000004060 metabolic process Effects 0.000 description 3
- 229960002847 prasterone Drugs 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 229960001712 testosterone propionate Drugs 0.000 description 3
- 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 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
- QZLYKIGBANMMBK-UGCZWRCOSA-N 5α-androstane group Chemical group [C@@H]12CCC[C@@]1(C)CC[C@H]1[C@H]2CC[C@H]2CCCC[C@]12C QZLYKIGBANMMBK-UGCZWRCOSA-N 0.000 description 2
- 206010055113 Breast cancer metastatic Diseases 0.000 description 2
- 102000007399 Nuclear hormone receptor Human genes 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 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 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001647 drug administration Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 231100000508 hormonal effect Toxicity 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 231100000682 maximum tolerated dose Toxicity 0.000 description 2
- 210000003205 muscle Anatomy 0.000 description 2
- 210000004940 nucleus Anatomy 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 238000002054 transplantation Methods 0.000 description 2
- 210000004291 uterus Anatomy 0.000 description 2
- BPOPNUSISSKIGI-UHFFFAOYSA-N 2-amino-4-chloro-2-phenylbutanoic acid Chemical compound ClCCC(C(=O)O)(C1=CC=CC=C1)N BPOPNUSISSKIGI-UHFFFAOYSA-N 0.000 description 1
- ARSRBNBHOADGJU-UHFFFAOYSA-N 7,12-dimethyltetraphene Chemical compound C1=CC2=CC=CC=C2C2=C1C(C)=C(C=CC=C1)C1=C2C ARSRBNBHOADGJU-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 208000010507 Adenocarcinoma of Lung Diseases 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- 206010003694 Atrophy Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 206010008342 Cervix carcinoma Diseases 0.000 description 1
- 108010077544 Chromatin Proteins 0.000 description 1
- VFZRZRDOXPRTSC-UHFFFAOYSA-N DMBA Natural products COC1=CC(OC)=CC(C=O)=C1 VFZRZRDOXPRTSC-UHFFFAOYSA-N 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 208000028018 Lymphocytic leukaemia Diseases 0.000 description 1
- 206010029350 Neurotoxicity Diseases 0.000 description 1
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- 108010007568 Protamines Proteins 0.000 description 1
- 102000007327 Protamines Human genes 0.000 description 1
- 206010039491 Sarcoma Diseases 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
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 206010044221 Toxic encephalopathy Diseases 0.000 description 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 description 1
- 229940030486 androgens Drugs 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
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- 229940124558 contraceptive agent Drugs 0.000 description 1
- 230000002254 contraceptive effect Effects 0.000 description 1
- 108091007930 cytoplasmic receptors Proteins 0.000 description 1
- 230000001086 cytosolic effect Effects 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- ADFOJJHRTBFFOF-RBRWEJTLSA-N estramustine phosphate Chemical compound ClCCN(CCCl)C(=O)OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)OP(O)(O)=O)[C@@H]4[C@@H]3CCC2=C1 ADFOJJHRTBFFOF-RBRWEJTLSA-N 0.000 description 1
- 229940011871 estrogen Drugs 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
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- 210000004907 gland Anatomy 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 201000003911 head and neck carcinoma Diseases 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 108091008039 hormone receptors Proteins 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000000366 juvenile effect Effects 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 201000005249 lung adenocarcinoma Diseases 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
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- 230000007246 mechanism Effects 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
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- 230000017074 necrotic cell death Effects 0.000 description 1
- 230000017066 negative regulation of growth Effects 0.000 description 1
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- 231100000228 neurotoxicity Toxicity 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 108020004017 nuclear receptors Proteins 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229950008679 protamine sulfate Drugs 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 210000001625 seminal vesicle Anatomy 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 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
- 239000012265 solid product Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 108010068815 steroid hormone 7-alpha-hydroxylase Proteins 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 230000007847 structural defect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- 229960003604 testosterone Drugs 0.000 description 1
- 150000003515 testosterones Chemical class 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 201000010653 vesiculitis Diseases 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU8400033 | 1984-06-27 | ||
| PCT/SU1984/000033 WO1986000311A1 (fr) | 1984-06-27 | 1984-06-27 | Derives de steroides de series d'androstane |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI860815A0 FI860815A0 (fi) | 1986-02-25 |
| FI860815L FI860815L (fi) | 1986-02-25 |
| FI84834B FI84834B (fi) | 1991-10-15 |
| FI84834C true FI84834C (fi) | 1992-01-27 |
Family
ID=21616852
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI860815A FI84834C (fi) | 1984-06-27 | 1986-02-25 | Foerfarande foer framstaellning av terapeutiskt anvaendbara steroidderivat av androstanserien. |
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) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1558472A (en) * | 1976-01-22 | 1980-01-03 | Leo Ab | 17-esters of 17- hydroxy gestogens |
| 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
Also Published As
| Publication number | Publication date |
|---|---|
| FI860815A0 (fi) | 1986-02-25 |
| GB8602936D0 (en) | 1986-03-12 |
| 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 |
| DE3490728C2 (de) | 1989-09-14 |
| CH666276A5 (de) | 1988-07-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: VSESOJUZNY ONKOLOGICHESKY NAUCHNY TSENTR Owner name: KHARKOVSKY NAUCHNO-ISSLEDOVATELSKY |