UA74592C2 - 4-halogenated 17-methylenesteroids , a method for producing thereof and a pharmaceutical composition containing these compounds - Google Patents
4-halogenated 17-methylenesteroids , a method for producing thereof and a pharmaceutical composition containing these compounds Download PDFInfo
- Publication number
- UA74592C2 UA74592C2 UA2003042852A UA2003042852A UA74592C2 UA 74592 C2 UA74592 C2 UA 74592C2 UA 2003042852 A UA2003042852 A UA 2003042852A UA 2003042852 A UA2003042852 A UA 2003042852A UA 74592 C2 UA74592 C2 UA 74592C2
- Authority
- UA
- Ukraine
- Prior art keywords
- chloroestr
- pseudohalogen
- general formula
- group
- methylene
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 51
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- 238000000034 method Methods 0.000 claims abstract description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 19
- 125000002577 pseudohalo group Chemical group 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 239000000010 aprotic solvent Substances 0.000 claims description 12
- 239000013543 active substance Substances 0.000 claims description 8
- -1 azido- Chemical class 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 230000003993 interaction Effects 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 230000005764 inhibitory process Effects 0.000 claims description 5
- CYDMYWHMDASKOT-QRXQDIEBSA-N (8r,9s,10r,13s,14s,17e)-4-chloro-17-(chloromethylidene)-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)(C(/CC4)=C/Cl)[C@@H]4[C@@H]3CCC2=C1Cl CYDMYWHMDASKOT-QRXQDIEBSA-N 0.000 claims description 4
- 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 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 239000003586 protic polar solvent Substances 0.000 claims description 4
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 3
- 201000004384 Alopecia Diseases 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 206010020112 Hirsutism Diseases 0.000 claims description 3
- 206010000496 acne Diseases 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 210000002307 prostate Anatomy 0.000 claims description 3
- NEDCCQPWOSRTHL-NMUAUPANSA-N (2e)-2-[(8r,9s,10r,13s,14s)-4-chloro-13-methyl-3-oxo-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ylidene]acetonitrile Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)(C(/CC4)=C/C#N)[C@@H]4[C@@H]3CCC2=C1Cl NEDCCQPWOSRTHL-NMUAUPANSA-N 0.000 claims description 2
- JCBFSZAXCWTSSI-QRXQDIEBSA-N (8r,9s,10r,13s,14s,17e)-17-(bromomethylidene)-4-chloro-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)(C(/CC4)=C/Br)[C@@H]4[C@@H]3CCC2=C1Cl JCBFSZAXCWTSSI-QRXQDIEBSA-N 0.000 claims description 2
- GWDCVGJWTTYHRW-BUNPSNNLSA-N (8r,9s,10r,13s,14s,17e)-17-(chloromethylidene)-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthrene-4-carbonitrile Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(/CC4)=C/Cl)[C@@H]4[C@@H]3CCC2=C1C#N GWDCVGJWTTYHRW-BUNPSNNLSA-N 0.000 claims description 2
- YMGACAXXGFIDDN-XDFMKLRHSA-N (8s,9s,10r,13s,14s,17e)-4-chloro-17-(chloromethylidene)-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-3-one Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(/CC4)=C/Cl)[C@@H]4[C@@H]3CCC2=C1Cl YMGACAXXGFIDDN-XDFMKLRHSA-N 0.000 claims description 2
- 231100000360 alopecia Toxicity 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 238000007142 ring opening reaction Methods 0.000 claims description 2
- 230000018044 dehydration Effects 0.000 claims 2
- 238000006297 dehydration reaction Methods 0.000 claims 2
- 239000012434 nucleophilic reagent Substances 0.000 claims 2
- MPOZXKYQQJUQEO-SICWGFIWSA-N (8r,9s,10r,13s,14s,17e)-4-chloro-17-ethylidene-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC2=C(Cl)C(=O)CC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CC\C(=C/C)[C@@]1(C)CC2 MPOZXKYQQJUQEO-SICWGFIWSA-N 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- SETMGIIITGNLAS-UHFFFAOYSA-N spizofurone Chemical compound O=C1C2=CC(C(=O)C)=CC=C2OC21CC2 SETMGIIITGNLAS-UHFFFAOYSA-N 0.000 claims 1
- 229950001870 spizofurone Drugs 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 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 abstract description 10
- 239000000126 substance Substances 0.000 abstract description 10
- 239000003098 androgen Substances 0.000 abstract description 8
- 239000000262 estrogen Substances 0.000 abstract description 6
- 229940011871 estrogen Drugs 0.000 abstract description 6
- 230000003054 hormonal effect Effects 0.000 abstract description 5
- 239000003112 inhibitor Substances 0.000 abstract description 5
- 239000000583 progesterone congener Substances 0.000 abstract description 5
- 229960003604 testosterone Drugs 0.000 abstract description 5
- 229940124558 contraceptive agent Drugs 0.000 abstract description 3
- 239000003433 contraceptive agent Substances 0.000 abstract description 3
- 210000000056 organ Anatomy 0.000 abstract description 3
- 230000003389 potentiating effect Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- 229910052786 argon Inorganic materials 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 239000007789 gas Substances 0.000 description 9
- 230000001681 protective effect Effects 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000012298 atmosphere Substances 0.000 description 8
- 239000003480 eluent Substances 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 239000012265 solid product Substances 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000009471 action Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 5
- 210000002149 gonad Anatomy 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 230000000757 progestagenic effect Effects 0.000 description 5
- 238000003828 vacuum filtration Methods 0.000 description 5
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound 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 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 229940095055 progestogen systemic hormonal contraceptives Drugs 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 206010036618 Premenstrual syndrome Diseases 0.000 description 3
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- 238000007911 parenteral administration Methods 0.000 description 3
- 238000004321 preservation Methods 0.000 description 3
- 230000001629 suppression Effects 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- KOUGPPSNDWPJPG-GWMKOSNLSA-N (8r,9s,10r,13s,14s,17e)-17-(bromomethylidene)-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)(C(/CC4)=C/Br)[C@@H]4[C@@H]3CCC2=C1 KOUGPPSNDWPJPG-GWMKOSNLSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- BFPYWIDHMRZLRN-UHFFFAOYSA-N 17alpha-ethynyl estradiol Natural products OC1=CC=C2C3CCC(C)(C(CC4)(O)C#C)C4C3CCC2=C1 BFPYWIDHMRZLRN-UHFFFAOYSA-N 0.000 description 2
- 229920000858 Cyclodextrin Polymers 0.000 description 2
- BFPYWIDHMRZLRN-SLHNCBLASA-N Ethinyl estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 BFPYWIDHMRZLRN-SLHNCBLASA-N 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 2
- 229940030486 androgens Drugs 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 229960002568 ethinylestradiol Drugs 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
- 210000003754 fetus Anatomy 0.000 description 2
- 210000004392 genitalia Anatomy 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 229940126601 medicinal product Drugs 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000012038 nucleophile Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 230000035935 pregnancy Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229960003387 progesterone Drugs 0.000 description 2
- 239000000186 progesterone Substances 0.000 description 2
- 208000017497 prostate disease Diseases 0.000 description 2
- 230000028327 secretion Effects 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- CPNOAXQKSRSFCC-GWMKOSNLSA-N (8r,9s,10r,13s,14s,17e)-17-(chloromethylidene)-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)(C(/CC4)=C/Cl)[C@@H]4[C@@H]3CCC2=C1 CPNOAXQKSRSFCC-GWMKOSNLSA-N 0.000 description 1
- 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 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 description 1
- UYIFTLBWAOGQBI-BZDYCCQFSA-N Benzhormovarine Chemical compound C([C@@H]1[C@@H](C2=CC=3)CC[C@]4([C@H]1CC[C@@H]4O)C)CC2=CC=3OC(=O)C1=CC=CC=C1 UYIFTLBWAOGQBI-BZDYCCQFSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- RSEPBGGWRJCQGY-RBRWEJTLSA-N Estradiol valerate Chemical compound C1CC2=CC(O)=CC=C2[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CCCC)[C@@]1(C)CC2 RSEPBGGWRJCQGY-RBRWEJTLSA-N 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010067572 Oestrogenic effect Diseases 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 108090000854 Oxidoreductases Proteins 0.000 description 1
- 102000004316 Oxidoreductases Human genes 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 208000004403 Prostatic Hyperplasia Diseases 0.000 description 1
- 108091007187 Reductases Proteins 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- RVKFQAJIXCZXQY-CBZIJGRNSA-N [(8r,9s,13s,14s)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-3-yl] sulfamate Chemical compound NS(=O)(=O)OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 RVKFQAJIXCZXQY-CBZIJGRNSA-N 0.000 description 1
- YXYXCSOJKUAPJI-ZBRFXRBCSA-N [(8r,9s,13s,14s,17s)-17-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] sulfamate Chemical compound NS(=O)(=O)OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 YXYXCSOJKUAPJI-ZBRFXRBCSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000000181 anti-adherent effect Effects 0.000 description 1
- 230000002280 anti-androgenic effect Effects 0.000 description 1
- 239000000051 antiandrogen Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229920002988 biodegradable polymer Polymers 0.000 description 1
- 239000004621 biodegradable polymer Substances 0.000 description 1
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 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
- 239000002775 capsule Substances 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229940035811 conjugated estrogen Drugs 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 210000000172 cytosol Anatomy 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229960001359 estradiol 3-benzoate Drugs 0.000 description 1
- 150000002159 estradiols Chemical class 0.000 description 1
- 230000001076 estrogenic effect Effects 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 230000035558 fertility Effects 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000005802 health problem Effects 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000000155 isotopic effect Effects 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- VOXZDWNPVJITMN-WKUFJEKOSA-N oestradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-WKUFJEKOSA-N 0.000 description 1
- 238000006772 olefination reaction Methods 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 102000003998 progesterone receptors Human genes 0.000 description 1
- 108090000468 progesterone receptors Proteins 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 230000021595 spermatogenesis Effects 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 239000006213 vaginal ring Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J13/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J13/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
- C07J13/007—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17 with double bond in position 17 (20)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/16—Masculine contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/18—Feminine contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/28—Antiandrogens
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/34—Gestagens
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Dermatology (AREA)
- Reproductive Health (AREA)
- Urology & Nephrology (AREA)
- Gynecology & Obstetrics (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10043846A DE10043846A1 (de) | 2000-09-04 | 2000-09-04 | 17-Methylensteroide, Verfahren zu deren Herstellung und diese Verbindung enthaltende pharmazeutische Zusammensetzungen |
| PCT/EP2001/009943 WO2002019971A1 (de) | 2000-09-04 | 2001-08-29 | 4-halogenierte 17-methylensteroide, verfahren zu deren herstellung und diese verbindungen enthaltende pharmazeutische zusammensetzungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA74592C2 true UA74592C2 (en) | 2006-01-16 |
Family
ID=7655148
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2003042852A UA74592C2 (en) | 2000-09-04 | 2001-08-29 | 4-halogenated 17-methylenesteroids , a method for producing thereof and a pharmaceutical composition containing these compounds |
Country Status (29)
| Country | Link |
|---|---|
| EP (1) | EP1423407B1 (zh) |
| JP (1) | JP2004513084A (zh) |
| KR (1) | KR100530816B1 (zh) |
| CN (1) | CN1262560C (zh) |
| AT (1) | ATE319733T1 (zh) |
| AU (2) | AU2002210470B2 (zh) |
| BG (1) | BG107594A (zh) |
| BR (1) | BR0113618A (zh) |
| CA (1) | CA2421302C (zh) |
| DE (2) | DE10043846A1 (zh) |
| DK (1) | DK1423407T3 (zh) |
| EA (1) | EA006387B1 (zh) |
| EE (1) | EE05186B1 (zh) |
| ES (1) | ES2260294T3 (zh) |
| HK (1) | HK1060135A1 (zh) |
| HR (1) | HRP20030256A2 (zh) |
| HU (1) | HUP0300936A3 (zh) |
| IL (2) | IL154666A0 (zh) |
| ME (1) | MEP14408A (zh) |
| MX (1) | MXPA03001912A (zh) |
| NO (1) | NO325012B1 (zh) |
| NZ (1) | NZ524485A (zh) |
| PL (1) | PL360669A1 (zh) |
| PT (1) | PT1423407E (zh) |
| RS (1) | RS50305B (zh) |
| SK (1) | SK286757B6 (zh) |
| UA (1) | UA74592C2 (zh) |
| WO (1) | WO2002019971A1 (zh) |
| ZA (1) | ZA200301715B (zh) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10141984A1 (de) * | 2001-08-28 | 2003-03-20 | Jenapharm Gmbh | Neue 17-Methylen-4-azasteroide |
| US7199115B2 (en) | 2004-04-19 | 2007-04-03 | Schering Ag | 17α-fluorosteroids, pharmaceutical compositions containing 17α-fluorosteroids and a method of making them |
| AT12800U1 (de) * | 2007-11-05 | 2012-11-15 | Bayer Schering Pharma Ag | Pharmazeutisches Präparat zur Verwendung bei der oralen Kontrazeption von Frauen mit Laktoseintoleranz |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2611773A (en) * | 1951-08-21 | 1952-09-23 | Upjohn Co | Estradiol 17-cyclopenetanepropionate |
| US3146239A (en) * | 1957-09-23 | 1964-08-25 | Syntex Corp | 4-halo-19-nor-progesterone |
| US3232960A (en) * | 1959-10-08 | 1966-02-01 | Upjohn Co | 3-keto-4-fluoro- and 3-keto-4,4-difluorosteroids and process |
| US3661940A (en) * | 1970-04-13 | 1972-05-09 | Sandoz Ag | Derivatives of 21-methyl-19-norpregnanes |
| US4389345A (en) * | 1981-10-09 | 1983-06-21 | G.D. Searle & Co. | 3-Oxoestra-17-acetonitrile and unsaturated analogs |
| US5994334A (en) * | 1997-02-05 | 1999-11-30 | University Of Maryland | Androgen synthesis inhibitors |
| WO2002000681A1 (en) * | 2000-06-27 | 2002-01-03 | Aventis Pharma S.A. | 20-fluoro-17(20)-vinyl steroids as inhibitors of c17-20-lyase and 5-alpha reductase |
-
2000
- 2000-09-04 DE DE10043846A patent/DE10043846A1/de not_active Ceased
-
2001
- 2001-08-29 MX MXPA03001912A patent/MXPA03001912A/es active IP Right Grant
- 2001-08-29 ES ES01978315T patent/ES2260294T3/es not_active Expired - Lifetime
- 2001-08-29 UA UA2003042852A patent/UA74592C2/uk unknown
- 2001-08-29 WO PCT/EP2001/009943 patent/WO2002019971A1/de active IP Right Grant
- 2001-08-29 IL IL15466601A patent/IL154666A0/xx unknown
- 2001-08-29 PT PT01978315T patent/PT1423407E/pt unknown
- 2001-08-29 EP EP01978315A patent/EP1423407B1/de not_active Expired - Lifetime
- 2001-08-29 AU AU2002210470A patent/AU2002210470B2/en not_active Ceased
- 2001-08-29 EA EA200300322A patent/EA006387B1/ru not_active IP Right Cessation
- 2001-08-29 JP JP2002524456A patent/JP2004513084A/ja active Pending
- 2001-08-29 HU HU0300936A patent/HUP0300936A3/hu unknown
- 2001-08-29 ME MEP-144/08A patent/MEP14408A/xx unknown
- 2001-08-29 NZ NZ524485A patent/NZ524485A/en unknown
- 2001-08-29 PL PL36066901A patent/PL360669A1/xx unknown
- 2001-08-29 DE DE50109175T patent/DE50109175D1/de not_active Expired - Lifetime
- 2001-08-29 KR KR10-2003-7003170A patent/KR100530816B1/ko not_active IP Right Cessation
- 2001-08-29 CA CA002421302A patent/CA2421302C/en not_active Expired - Fee Related
- 2001-08-29 AT AT01978315T patent/ATE319733T1/de not_active IP Right Cessation
- 2001-08-29 RS YUP-164/03A patent/RS50305B/sr unknown
- 2001-08-29 SK SK244-2003A patent/SK286757B6/sk not_active IP Right Cessation
- 2001-08-29 BR BR0113618-6A patent/BR0113618A/pt not_active IP Right Cessation
- 2001-08-29 AU AU1047002A patent/AU1047002A/xx active Pending
- 2001-08-29 DK DK01978315T patent/DK1423407T3/da active
- 2001-08-29 CN CNB018151345A patent/CN1262560C/zh not_active Expired - Fee Related
- 2001-08-29 EE EEP200300087A patent/EE05186B1/xx not_active IP Right Cessation
-
2003
- 2003-02-27 IL IL154666A patent/IL154666A/en not_active IP Right Cessation
- 2003-02-27 BG BG107594A patent/BG107594A/bg unknown
- 2003-02-28 ZA ZA200301715A patent/ZA200301715B/en unknown
- 2003-03-03 NO NO20030989A patent/NO325012B1/no not_active IP Right Cessation
- 2003-04-04 HR HR20030256A patent/HRP20030256A2/hr not_active Application Discontinuation
-
2004
- 2004-04-27 HK HK04102956A patent/HK1060135A1/xx not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6855836B2 (en) | 17-Methylene steroids, process for their production and pharmaceutical compositions that contain these compounds | |
| RU2386637C2 (ru) | 15β-ЗАМЕЩЕННЫЕ СТЕРОИДЫ С ИЗБИРАТЕЛЬНОЙ ЭСТРОГЕННОЙ АКТИВНОСТЬЮ | |
| EA002623B1 (ru) | 11β-ГАЛОГЕН-7α-ЗАМЕЩЕННЫЕ ЭСТРАТРИЕНЫ, СПОСОБ ПОЛУЧЕНИЯ ФАРМАЦЕВТИЧЕСКИХ ПРЕПАРАТОВ, СОДЕРЖАЩИХ ЭТИ 11β-ГАЛОГЕН-7α-ЗАМЕЩЕННЫЕ ЭСТРАТРИЕНЫ, И ИХ ПРИМЕНЕНИЕ ДЛЯ ИЗГОТОВЛЕНИЯ ЛЕКАРСТВЕННЫХ СРЕДСТВ | |
| KR0142881B1 (ko) | 성스테로이드 활성 억제용 에스트로겐 핵유도체 | |
| KR19990081895A (ko) | 19-노르-프레그넨 유도체 및 이를 함유하는 약학적 조성물 | |
| NO329563B1 (no) | 9-alfa-substituerte ostratriener som selektivt aktive ostrogener, farmasoytiske preparater som inneholder forbindelsene, samt anvendelse derav til fremstilling av farmasoytiske midler | |
| US7199115B2 (en) | 17α-fluorosteroids, pharmaceutical compositions containing 17α-fluorosteroids and a method of making them | |
| UA74592C2 (en) | 4-halogenated 17-methylenesteroids , a method for producing thereof and a pharmaceutical composition containing these compounds | |
| ES2393942T3 (es) | 16,ALFA-FLUORO-ESTRATIENOS 8-BETA- sustituidos en calidad de estrógenos selectivamente activos | |
| IE902726A1 (en) | 14,17ó-etheno- and -ethanoestratrienes, processes for the¹preparation of these compounds, as well as their use for the¹production of medicinal agents | |
| US8026229B2 (en) | Antitumor-active 2-alkoxyestradiol sulfamates | |
| JP2007532688A (ja) | １７α−フルオロ−１７β−ヒドロキシイミノメチルステロイド、それらを製造する方法および前記化合物を含んでなる医薬組成物 | |
| US20040142915A1 (en) | 11beta-short chain substituted estradiol analogs and their use in the treatment of menopausal symptoms and estrogen sensitive cancer | |
| AU2006211907A1 (en) | Nandrolone 17beta-carbonates | |
| US7375098B2 (en) | 8β-vinyl-11β-(ω-substituted)alkyl-estra-1,3,5(10)-trienes | |
| CZ20024014A3 (cs) | Steroidní derivát | |
| NZ536882A (en) | 9-Alpha-substituted estratrienes as selectively active estrogens | |
| AU3405600A (en) | Sex steroid activity inhibitors | |
| MX2007002815A (es) | Esteroides substituidos pro 15( que tienen actividad. |