SK83099A3 - Steroids substituted in position 11, method of preparation, application as medicines and pharmaceutical compositions containing them - Google Patents

Steroids substituted in position 11, method of preparation, application as medicines and pharmaceutical compositions containing them Download PDF

Info

Publication number: SK83099A3
Authority: SK; Slovakia
Prior art keywords: formula; compounds; phenyl; ethoxy; carbon atoms
Prior art date: 1996-12-23

Application number

SK830-99A

Other languages

English (en)

Slovak (sk)

Inventor

Yamina Bouali

Francois Nique

Jean-Georges Teutsch

De Velde Patrick Van

Original Assignee

Hoechst Marion Roussel Inc

Priority date (The priority date 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 date listed.)

1996-12-23

Filing date

1997-12-22

Publication date

2000-01-18

1997-12-22 Application filed by Hoechst Marion Roussel Inc filed Critical Hoechst Marion Roussel Inc

2000-01-18 Publication of SK83099A3 publication Critical patent/SK83099A3/sk

Links

239000003814 drug Substances 0.000 title claims abstract description 13
238000000034 method Methods 0.000 title claims abstract description 13
239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 7
238000002360 preparation method Methods 0.000 title claims description 13
150000003431 steroids Chemical group 0.000 title description 6
229940079593 drug Drugs 0.000 title 1
150000003839 salts Chemical class 0.000 claims abstract description 19
-1 steroid compounds Chemical class 0.000 claims abstract description 16
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 8
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 46
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
239000002253 acid Substances 0.000 claims description 18
125000000217 alkyl group Chemical group 0.000 claims description 17
125000004432 carbon atom Chemical group C* 0.000 claims description 17
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 15
230000001076 estrogenic effect Effects 0.000 claims description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
125000003870 2-(1-piperidinyl)ethoxy group Chemical group [*]OC([H])([H])C([H])([H])N1C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 9
208000026310 Breast neoplasm Diseases 0.000 claims description 9
208000001132 Osteoporosis Diseases 0.000 claims description 9
125000003118 aryl group Chemical group 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 8
230000002265 prevention Effects 0.000 claims description 7
150000007513 acids Chemical class 0.000 claims description 6
230000009245 menopause Effects 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
210000004291 uterus Anatomy 0.000 claims description 6
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
238000005886 esterification reaction Methods 0.000 claims description 5
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000000304 alkynyl group Chemical group 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
125000005842 heteroatom Chemical group 0.000 claims description 3
238000002657 hormone replacement therapy Methods 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
125000002950 monocyclic group Chemical group 0.000 claims description 3
150000002902 organometallic compounds Chemical class 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
239000003638 chemical reducing agent Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000004585 polycyclic heterocycle group Chemical group 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
239000011593 sulfur Chemical group 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
239000000654 additive Substances 0.000 abstract 1
230000000996 additive effect Effects 0.000 abstract 1
150000002391 heterocyclic compounds Chemical class 0.000 abstract 1
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
239000000047 product Substances 0.000 description 27
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 17
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
210000000988 bone and bone Anatomy 0.000 description 14
230000000694 effects Effects 0.000 description 13
241001465754 Metazoa Species 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
229930182833 estradiol Natural products 0.000 description 10
229960005309 estradiol Drugs 0.000 description 10
239000000243 solution Substances 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
241000700159 Rattus Species 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
238000010521 absorption reaction Methods 0.000 description 7
239000003480 eluent Substances 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
239000002904 solvent Substances 0.000 description 7
206010006187 Breast cancer Diseases 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
230000010261 cell growth Effects 0.000 description 6
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
229940011871 estrogen Drugs 0.000 description 5
239000000262 estrogen Substances 0.000 description 5
238000012360 testing method Methods 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
LGHBWDKMGOIZKH-CBZIJGRNSA-N 3-Deoxyestrone Chemical compound C1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 LGHBWDKMGOIZKH-CBZIJGRNSA-N 0.000 description 4
206010017076 Fracture Diseases 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
230000001833 anti-estrogenic effect Effects 0.000 description 4
239000012298 atmosphere Substances 0.000 description 4
210000000481 breast Anatomy 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
125000000623 heterocyclic group Chemical group 0.000 description 4
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 4
230000002829 reductive effect Effects 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
206010065687 Bone loss Diseases 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
238000003556 assay Methods 0.000 description 3
CELPHAGZKFMOMR-UHFFFAOYSA-N azanium;dichloromethane;methanol;hydroxide Chemical compound [NH4+].[OH-].OC.ClCCl CELPHAGZKFMOMR-UHFFFAOYSA-N 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
239000012043 crude product Substances 0.000 description 3
208000035475 disorder Diseases 0.000 description 3
230000012010 growth Effects 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
239000000203 mixture Substances 0.000 description 3
230000002062 proliferating effect Effects 0.000 description 3
210000002966 serum Anatomy 0.000 description 3
239000000725 suspension Substances 0.000 description 3
239000003981 vehicle Substances 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
208000029725 Metabolic bone disease Diseases 0.000 description 2
206010049088 Osteopenia Diseases 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
239000000556 agonist Substances 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
210000004027 cell Anatomy 0.000 description 2
230000004663 cell proliferation Effects 0.000 description 2
230000002526 effect on cardiovascular system Effects 0.000 description 2
230000002357 endometrial effect Effects 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
230000007774 longterm Effects 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
239000011707 mineral Substances 0.000 description 2
210000003205 muscle Anatomy 0.000 description 2
210000000056 organ Anatomy 0.000 description 2
210000001672 ovary Anatomy 0.000 description 2
230000003449 preventive effect Effects 0.000 description 2
238000006722 reduction reaction Methods 0.000 description 2
238000009256 replacement therapy Methods 0.000 description 2
238000010898 silica gel chromatography Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
208000024891 symptom Diseases 0.000 description 2
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
210000004881 tumor cell Anatomy 0.000 description 2
DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 description 1
FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 1
GYLMCBOAXJVARF-UHFFFAOYSA-N 3-azabicyclo[2.2.1]heptane Chemical compound C1C2CCC1NC2 GYLMCBOAXJVARF-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
208000003200 Adenoma Diseases 0.000 description 1
201000000736 Amenorrhea Diseases 0.000 description 1
206010001928 Amenorrhoea Diseases 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
206010003694 Atrophy Diseases 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
201000009030 Carcinoma Diseases 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 1
MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 1
239000006144 Dulbecco’s modiﬁed Eagle's medium Substances 0.000 description 1
DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 description 1
208000008899 Habitual abortion Diseases 0.000 description 1
101000610640 Homo sapiens U4/U6 small nuclear ribonucleoprotein Prp3 Proteins 0.000 description 1
208000033830 Hot Flashes Diseases 0.000 description 1
206010060800 Hot flush Diseases 0.000 description 1
208000008454 Hyperhidrosis Diseases 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
240000007472 Leucaena leucocephala Species 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
206010027476 Metastases Diseases 0.000 description 1
BELBBZDIHDAJOR-UHFFFAOYSA-N Phenolsulfonephthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2S(=O)(=O)O1 BELBBZDIHDAJOR-UHFFFAOYSA-N 0.000 description 1
206010060862 Prostate cancer Diseases 0.000 description 1
101001110823 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) 60S ribosomal protein L6-A Proteins 0.000 description 1
101000712176 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) 60S ribosomal protein L6-B Proteins 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
102100040374 U4/U6 small nuclear ribonucleoprotein Prp3 Human genes 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
230000001270 agonistic effect Effects 0.000 description 1
231100000540 amenorrhea Toxicity 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
230000001028 anti-proliverative effect Effects 0.000 description 1
230000001395 anti-uterotrophic effect Effects 0.000 description 1
239000008135 aqueous vehicle Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
230000037444 atrophy Effects 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Substances OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
201000007295 breast benign neoplasm Diseases 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000006143 cell culture medium Substances 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
VYLVYHXQOHJDJL-UHFFFAOYSA-K cerium trichloride Chemical compound Cl[Ce](Cl)Cl VYLVYHXQOHJDJL-UHFFFAOYSA-K 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
235000012000 cholesterol Nutrition 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
239000002285 corn oil Substances 0.000 description 1
235000005687 corn oil Nutrition 0.000 description 1
229960004544 cortisone Drugs 0.000 description 1
239000006071 cream Substances 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
239000012351 deprotecting agent Substances 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000009547 dual-energy X-ray absorptiometry Methods 0.000 description 1
230000004821 effect on bone Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
201000006828 endometrial hyperplasia Diseases 0.000 description 1
230000032050 esterification Effects 0.000 description 1
239000000328 estrogen antagonist Substances 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
235000019197 fats Nutrition 0.000 description 1
235000013305 food Nutrition 0.000 description 1
230000002538 fungal effect Effects 0.000 description 1
239000000499 gel Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000008187 granular material Substances 0.000 description 1
239000003102 growth factor Substances 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
239000005556 hormone Substances 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
239000007943 implant Substances 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
125000001041 indolyl group Chemical group 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
208000014674 injury Diseases 0.000 description 1
238000011835 investigation Methods 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
230000002147 killing effect Effects 0.000 description 1
239000008101 lactose Substances 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
150000002642 lithium compounds Chemical class 0.000 description 1
150000002681 magnesium compounds Chemical class 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000005259 measurement Methods 0.000 description 1
239000002609 medium Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
DNMCNCTUMLBHKO-UHFFFAOYSA-N methyl(trifluoromethyl)silane Chemical compound C[SiH2]C(F)(F)F DNMCNCTUMLBHKO-UHFFFAOYSA-N 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
239000004005 microsphere Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229940105631 nembutal Drugs 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000002687 nonaqueous vehicle Substances 0.000 description 1
239000002674 ointment Substances 0.000 description 1
238000009806 oophorectomy Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
230000002611 ovarian Effects 0.000 description 1
210000003101 oviduct Anatomy 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
239000008188 pellet Substances 0.000 description 1
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229960003531 phenolsulfonphthalein Drugs 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000000962 progestomimetic effect Effects 0.000 description 1
230000035755 proliferation Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
201000001514 prostate carcinoma Diseases 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000002755 pyrazolinyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
208000034213 recurrent susceptibility to 1 pregnancy loss Diseases 0.000 description 1
238000010992 reflux Methods 0.000 description 1
210000004994 reproductive system Anatomy 0.000 description 1
210000005000 reproductive tract Anatomy 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
210000004872 soft tissue Anatomy 0.000 description 1
241000894007 species Species 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000001629 suppression Effects 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
230000035900 sweating Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003826 tablet Substances 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
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000002769 thiazolinyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
230000001131 transforming effect Effects 0.000 description 1
230000008733 trauma Effects 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
230000002485 urinary effect Effects 0.000 description 1
230000001836 utereotrophic effect Effects 0.000 description 1
210000001215 vagina Anatomy 0.000 description 1
238000005303 weighing Methods 0.000 description 1
230000004584 weight gain Effects 0.000 description 1
235000019786 weight gain Nutrition 0.000 description 1
238000009736 wetting Methods 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
- 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
- C07J41/0077—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom
- C07J41/0083—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom substituted in position 11-beta by an optionally substituted phenyl group not further condensed with other rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
- 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
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/32—Antioestrogens

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Physical Education & Sports Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Orthopedic Medicine & Surgery (AREA)
Rheumatology (AREA)
Diabetes (AREA)
Endocrinology (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

SK830-99A 1996-12-23 1997-12-22 Steroids substituted in position 11, method of preparation, application as medicines and pharmaceutical compositions containing them SK83099A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9615829A FR2757519B1 (fr)	1996-12-23	1996-12-23	Steroides substitues en position 11, leur procede de preparation, leur application comme medicament et les compositions pharmaceutiques les renfermant
PCT/FR1997/002379 WO1998028324A1 (fr)	1996-12-23	1997-12-22	Steroides substitues en position 11, leur procede de preparation, leur application comme medicaments et les compositions pharmaceutiques les renfermant

Publications (1)

Publication Number	Publication Date
SK83099A3 true SK83099A3 (en)	2000-01-18

Family

ID=9498983

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK830-99A SK83099A3 (en)	1996-12-23	1997-12-22	Steroids substituted in position 11, method of preparation, application as medicines and pharmaceutical compositions containing them

Country Status (33)

Country	Link
US (3)	US6207657B1 (de)
EP (1)	EP0946585B1 (de)
JP (1)	JP4376319B2 (de)
KR (1)	KR20000062288A (de)
CN (1)	CN1247541A (de)
AP (1)	AP9901567A0 (de)
AR (1)	AR010857A1 (de)
AT (1)	ATE216396T1 (de)
AU (1)	AU726350B2 (de)
BR (1)	BR9714433A (de)
CA (1)	CA2275955A1 (de)
CZ (1)	CZ227899A3 (de)
DE (1)	DE69712095T2 (de)
DK (1)	DK0946585T3 (de)
EA (1)	EA001868B1 (de)
ES (1)	ES2174329T3 (de)
FR (1)	FR2757519B1 (de)
HR (1)	HRP970711B1 (de)
HU (1)	HUP0001447A3 (de)
ID (1)	ID22627A (de)
IL (1)	IL130509A0 (de)
NO (1)	NO313333B1 (de)
NZ (1)	NZ336224A (de)
PL (1)	PL334124A1 (de)
PT (1)	PT946585E (de)
SI (1)	SI0946585T1 (de)
SK (1)	SK83099A3 (de)
TR (1)	TR199901453T2 (de)
TW (1)	TW492974B (de)
UA (1)	UA54483C2 (de)
WO (1)	WO1998028324A1 (de)
YU (1)	YU29299A (de)
ZA (1)	ZA9711324B (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2757519B1 (fr) *	1996-12-23	1999-06-11	Hoechst Marion Roussel Inc	Steroides substitues en position 11, leur procede de preparation, leur application comme medicament et les compositions pharmaceutiques les renfermant
FR2780060B1 (fr)	1998-06-23	2000-08-04	Hoechst Marion Roussel Inc	Nouveaux 19-nor steroides 17-halogenes, procede et intermediaires de preparation, application comme medicaments et compositions pharmaceutiques les renfermant
DE19929715A1 (de)	1999-06-24	2000-12-28	Schering Ag	11ß-langkettig-substituierte Estratriene, Verfahren zur Herstellung , pharmazeutische Präparate, die diese 11ß-langkettig-substituierten Estratriene enthalten, sowie deren Verwendung zur Herstellung von Arzneimitteln
FR2826004B1 (fr) *	2001-06-13	2008-03-28	Aventis Pharma Sa	Procede de preparation de derives estrogenes
FR2854402B1 (fr) *	2003-04-29	2008-07-04	Aventis Pharma Sa	Nouveau procede et intermediaires de preparation de composes 19-nor-steroides

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2640977A2 (en) *	1982-06-11	1990-06-29	Roussel Uclaf	New position-11 substituted 19-norsteroids and their application as medicinal products.
US4859585A (en) *	1986-04-17	1989-08-22	Trustees Of Tufts College	In-vitro methods for identifying compositions which are agonists and antagonists of estrogens
FR2643638B1 (fr) *	1989-02-24	1991-06-14	Roussel Uclaf	Nouveaux 19-nor steroides ayant en position 11beta une chaine carbonee comportant une fonction amide ou carbamate, leur procede de preparation et les intermediaires de ce procede, leur application comme medicaments et les compositions pharmaceutiques les contenant
JP3377856B2 (ja) *	1993-03-25	2003-02-17	イスクラ産業株式会社	骨吸収抑制・骨形成促進化合物
DE4329867C1 (de) *	1993-09-03	1994-09-15	Siemens Ag	Stromspiegel
FR2757519B1 (fr) *	1996-12-23	1999-06-11	Hoechst Marion Roussel Inc	Steroides substitues en position 11, leur procede de preparation, leur application comme medicament et les compositions pharmaceutiques les renfermant
FR2757399B1 (fr) *	1996-12-23	1999-12-17	Hoechst Marion Roussel Inc	Application de composes steroides substitues en 11 pour la fabrication de medicaments ayant une activite estrogene dissociee
FR2761992B1 (fr) *	1997-04-09	1999-06-11	Hoechst Marion Roussel Inc	Nouveaux steroides 4-halogenes, leur procede et intermediaires de preparation, leur application comme medicaments et les compositions pharmaceutiques les renfermant
FR2771096B1 (fr) *	1997-11-17	2000-08-11	Hoechst Marion Roussel Inc	Nouveaux 19-nor steroides, substitues en position 11beta, procede et intermediaires de preparation, application comme medicaments et compositions pharmaceutiques les renfermant

1996
- 1996-12-23 FR FR9615829A patent/FR2757519B1/fr not_active Expired - Fee Related
1997
- 1997-12-17 ZA ZA9711324A patent/ZA9711324B/xx unknown
- 1997-12-22 ES ES97952972T patent/ES2174329T3/es not_active Expired - Lifetime
- 1997-12-22 US US09/331,823 patent/US6207657B1/en not_active Expired - Lifetime
- 1997-12-22 DK DK97952972T patent/DK0946585T3/da active
- 1997-12-22 ID IDW990573A patent/ID22627A/id unknown
- 1997-12-22 SI SI9730353T patent/SI0946585T1/xx unknown
- 1997-12-22 PL PL97334124A patent/PL334124A1/xx unknown
- 1997-12-22 SK SK830-99A patent/SK83099A3/sk unknown
- 1997-12-22 CA CA002275955A patent/CA2275955A1/fr not_active Abandoned
- 1997-12-22 YU YU29299A patent/YU29299A/sh unknown
- 1997-12-22 CZ CZ992278A patent/CZ227899A3/cs unknown
- 1997-12-22 AT AT97952972T patent/ATE216396T1/de not_active IP Right Cessation
- 1997-12-22 CN CN97181921A patent/CN1247541A/zh active Pending
- 1997-12-22 KR KR1019997005685A patent/KR20000062288A/ko not_active Withdrawn
- 1997-12-22 EA EA199900588A patent/EA001868B1/ru not_active IP Right Cessation
- 1997-12-22 EP EP97952972A patent/EP0946585B1/de not_active Expired - Lifetime
- 1997-12-22 JP JP52847398A patent/JP4376319B2/ja not_active Expired - Fee Related
- 1997-12-22 IL IL13050997A patent/IL130509A0/xx unknown
- 1997-12-22 BR BR9714433-9A patent/BR9714433A/pt not_active IP Right Cessation
- 1997-12-22 AU AU56678/98A patent/AU726350B2/en not_active Ceased
- 1997-12-22 HU HU0001447A patent/HUP0001447A3/hu unknown
- 1997-12-22 AP APAP/P/1999/001567A patent/AP9901567A0/en unknown
- 1997-12-22 DE DE69712095T patent/DE69712095T2/de not_active Expired - Lifetime
- 1997-12-22 TR TR1999/01453T patent/TR199901453T2/xx unknown
- 1997-12-22 WO PCT/FR1997/002379 patent/WO1998028324A1/fr not_active Ceased
- 1997-12-22 PT PT97952972T patent/PT946585E/pt unknown
- 1997-12-22 UA UA99074263A patent/UA54483C2/uk unknown
- 1997-12-22 NZ NZ336224A patent/NZ336224A/en unknown
- 1997-12-23 HR HR970711A patent/HRP970711B1/xx not_active IP Right Cessation
- 1997-12-23 AR ARP970106163A patent/AR010857A1/es unknown
1998
- 1998-02-06 TW TW086119813A patent/TW492974B/zh active
1999
- 1999-06-23 NO NO19993125A patent/NO313333B1/no unknown
2000
- 2000-06-13 US US09/592,710 patent/US6482813B1/en not_active Expired - Lifetime
2002
- 2002-02-14 US US10/075,364 patent/US6541464B2/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
ID22627A (id)	1999-12-02
FR2757519A1 (fr)	1998-06-26
TW492974B (en)	2002-07-01
DK0946585T3 (da)	2002-08-05
KR20000062288A (ko)	2000-10-25
AU5667898A (en)	1998-07-17
NO993125L (no)	1999-08-20
HUP0001447A1 (hu)	2000-11-28
SI0946585T1 (en)	2002-10-31
US6207657B1 (en)	2001-03-27
EP0946585B1 (de)	2002-04-17
PL334124A1 (en)	2000-02-14
US6541464B2 (en)	2003-04-01
JP4376319B2 (ja)	2009-12-02
EP0946585A1 (de)	1999-10-06
CA2275955A1 (fr)	1998-07-02
US20020198374A1 (en)	2002-12-26
FR2757519B1 (fr)	1999-06-11
NZ336224A (en)	2001-02-23
DE69712095T2 (de)	2002-11-14
PT946585E (pt)	2002-09-30
JP2001507010A (ja)	2001-05-29
HRP970711A2 (en)	1998-10-31
EA001868B1 (ru)	2001-10-22
WO1998028324A1 (fr)	1998-07-02
YU29299A (sh)	2001-05-28
IL130509A0 (en)	2000-06-01
AU726350B2 (en)	2000-11-02
UA54483C2 (uk)	2003-03-17
HRP970711B1 (en)	2002-04-30
ES2174329T3 (es)	2002-11-01
NO313333B1 (no)	2002-09-16
HUP0001447A3 (en)	2001-03-28
ATE216396T1 (de)	2002-05-15
CZ227899A3 (cs)	1999-09-15
AR010857A1 (es)	2000-07-12
TR199901453T2 (xx)	1999-08-23
AP9901567A0 (en)	1999-06-30
ZA9711324B (en)	1999-01-19
CN1247541A (zh)	2000-03-15
BR9714433A (pt)	2000-05-02
DE69712095D1 (de)	2002-05-23
EA199900588A1 (ru)	2000-02-28
US6482813B1 (en)	2002-11-19
NO993125D0 (no)	1999-06-23

Publication	Publication Date	Title
JP2753562B2 (ja)	1998-05-20	新規な１１−ベンズアルドキシム−エストラ−ジエン誘導体とその製造方法、及びその化合物を含有する医薬製剤
JP4959276B2 (ja)	2012-06-20	新規な抗エストロゲンステロイド、ならびに関連の薬学的組成物および使用法
US20020032180A1 (en)	2002-03-14	Novel anti-estrogenic steroids, and associated pharmaceutical compositions and methods of use
JPH07149790A (ja)	1995-06-13	新規な１１−ベンズアルドキシム−１７β−メトキシ−１７α−メトキシメチル−エストラジエン誘導体、その製法およびその物質を含有する医薬製剤
JP2005539016A (ja)	2005-12-22	女性用受胎調節及びホルモン置換療法のための高められた抗ゴナドトロピン活性を有するプロゲステロン受容体モジュレーター
SK83099A3 (en)	2000-01-18	Steroids substituted in position 11, method of preparation, application as medicines and pharmaceutical compositions containing them
DE69806473T2 (de)	2003-02-13	Neue 4-halogenierte steroide, ein verfahren und zwischenprodukten zu ihrer herstellung, ihre verwendung als medikamenten und pharmazeutische zusammensetzungen davon
DE69811393T2 (de)	2003-08-28	Neue 19-nor 11-beta-substituierte steroide, ein verfahren zu ihrer herstellung sowie zwischenprodukten dieses verfahrens und ihre anwendung als medikamenten
JP4263264B2 (ja)	2009-05-13	解離したエストロゲン活性を有する薬剤を製造するための１１位置換ステロイド化合物の用途
WO1998028324A9 (fr)	1998-10-29	Steroides substitues en position 11, leur procede de preparation, leur application comme medicaments et les compositions pharmaceutiques les renfermant
JP4509380B2 (ja)	2010-07-21	新規の１７−ハロゲン化−１９−ノルステロイド、それらの製造方法及び中間体、それらの医薬としての使用並びにそれらを含有する製薬組成物
MXPA99005841A (en)	2000-01-01	Steroids substituted in position 11, method of preparation, application as medicines and pharmaceutical compositions containing them
MXPA00004712A (en)	2001-09-07	NOVEL 19-NOR STEROIDS SUBSTITUTED IN POSITION 11&bgr;, PREPARATION METHOD AND INTERMEDIATES, APPLICATION AS MEDICINES AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM