HRP20000269A2 - Anti-estrogen plus progestin containing oral contraceptives - Google Patents
Anti-estrogen plus progestin containing oral contraceptives Download PDFInfo
- Publication number
- HRP20000269A2 HRP20000269A2 HR20000269A HRP20000269A HRP20000269A2 HR P20000269 A2 HRP20000269 A2 HR P20000269A2 HR 20000269 A HR20000269 A HR 20000269A HR P20000269 A HRP20000269 A HR P20000269A HR P20000269 A2 HRP20000269 A2 HR P20000269A2
- Authority
- HR
- Croatia
- Prior art keywords
- ethoxy
- benzyl
- phenyl
- methyl
- indol
- Prior art date
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- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical class 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 title claims description 71
- 239000000328 estrogen antagonist Substances 0.000 title claims description 35
- 229940046836 anti-estrogen Drugs 0.000 title claims description 33
- 230000001833 anti-estrogenic effect Effects 0.000 title claims description 33
- 229940127234 oral contraceptive Drugs 0.000 title description 9
- 239000003539 oral contraceptive agent Substances 0.000 title description 9
- 239000000583 progesterone congener Substances 0.000 title description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 39
- 229960003387 progesterone Drugs 0.000 claims description 36
- 239000000186 progesterone Substances 0.000 claims description 34
- WWYNJERNGUHSAO-XUDSTZEESA-N (+)-Norgestrel Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](CC)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 WWYNJERNGUHSAO-XUDSTZEESA-N 0.000 claims description 19
- 229960004400 levonorgestrel Drugs 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 9
- 239000003433 contraceptive agent Substances 0.000 claims description 9
- 230000001836 utereotrophic effect Effects 0.000 claims description 9
- 230000027758 ovulation cycle Effects 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 239000003418 antiprogestin Substances 0.000 claims description 6
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 6
- 230000002254 contraceptive effect Effects 0.000 claims description 6
- 230000003623 progesteronic effect Effects 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- IMONTRJLAWHYGT-ZCPXKWAGSA-N Norethindrone Acetate Chemical compound C1CC2=CC(=O)CC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CC[C@](C#C)(OC(=O)C)[C@@]1(C)CC2 IMONTRJLAWHYGT-ZCPXKWAGSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 229960000978 cyproterone acetate Drugs 0.000 claims description 5
- UWFYSQMTEOIJJG-FDTZYFLXSA-N cyproterone acetate Chemical compound C1=C(Cl)C2=CC(=O)[C@@H]3C[C@@H]3[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 UWFYSQMTEOIJJG-FDTZYFLXSA-N 0.000 claims description 5
- 229960004976 desogestrel Drugs 0.000 claims description 5
- RPLCPCMSCLEKRS-BPIQYHPVSA-N desogestrel Chemical compound C1CC[C@@H]2[C@H]3C(=C)C[C@](CC)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 RPLCPCMSCLEKRS-BPIQYHPVSA-N 0.000 claims description 5
- 229960003309 dienogest Drugs 0.000 claims description 5
- AZFLJNIPTRTECV-FUMNGEBKSA-N dienogest Chemical compound C1CC(=O)C=C2CC[C@@H]([C@H]3[C@@](C)([C@](CC3)(O)CC#N)CC3)C3=C21 AZFLJNIPTRTECV-FUMNGEBKSA-N 0.000 claims description 5
- METQSPRSQINEEU-UHFFFAOYSA-N dihydrospirorenone Natural products CC12CCC(C3(CCC(=O)C=C3C3CC33)C)C3C1C1CC1C21CCC(=O)O1 METQSPRSQINEEU-UHFFFAOYSA-N 0.000 claims description 5
- 229960004845 drospirenone Drugs 0.000 claims description 5
- METQSPRSQINEEU-HXCATZOESA-N drospirenone Chemical compound C([C@]12[C@H]3C[C@H]3[C@H]3[C@H]4[C@@H]([C@]5(CCC(=O)C=C5[C@@H]5C[C@@H]54)C)CC[C@@]31C)CC(=O)O2 METQSPRSQINEEU-HXCATZOESA-N 0.000 claims description 5
- GCKFUYQCUCGESZ-BPIQYHPVSA-N etonogestrel Chemical compound O=C1CC[C@@H]2[C@H]3C(=C)C[C@](CC)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 GCKFUYQCUCGESZ-BPIQYHPVSA-N 0.000 claims description 5
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 5
- 229960005352 gestodene Drugs 0.000 claims description 5
- SIGSPDASOTUPFS-XUDSTZEESA-N gestodene Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](CC)([C@](C=C4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 SIGSPDASOTUPFS-XUDSTZEESA-N 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 229940053934 norethindrone Drugs 0.000 claims description 5
- 229960001652 norethindrone acetate Drugs 0.000 claims description 5
- VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 claims description 5
- 229960000417 norgestimate Drugs 0.000 claims description 5
- KIQQMECNKUGGKA-NMYWJIRASA-N norgestimate Chemical compound O/N=C/1CC[C@@H]2[C@H]3CC[C@](CC)([C@](CC4)(OC(C)=O)C#C)[C@@H]4[C@@H]3CCC2=C\1 KIQQMECNKUGGKA-NMYWJIRASA-N 0.000 claims description 5
- 229950006466 osaterone Drugs 0.000 claims description 5
- ZLLOIFNEEWYATC-XMUHMHRVSA-N osaterone Chemical compound C1=C(Cl)C2=CC(=O)OC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)C)(O)[C@@]1(C)CC2 ZLLOIFNEEWYATC-XMUHMHRVSA-N 0.000 claims description 5
- 229950008546 trimegestone Drugs 0.000 claims description 5
- JUNDJWOLDSCTFK-MTZCLOFQSA-N trimegestone Chemical compound C1CC2=CC(=O)CCC2=C2[C@@H]1[C@@H]1CC[C@@](C(=O)[C@@H](O)C)(C)[C@@]1(C)CC2 JUNDJWOLDSCTFK-MTZCLOFQSA-N 0.000 claims description 5
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 150000003973 alkyl amines Chemical class 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- INEHJXCWEVNEDZ-LUDNRVPPSA-N (2s,3s)-2,3-dihydroxybutanedioic acid;(5r,6s)-6-phenyl-5-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-5,6,7,8-tetrahydronaphthalen-2-ol Chemical compound OC(=O)[C@@H](O)[C@H](O)C(O)=O.C1([C@@H]2[C@@H](C3=CC=C(C=C3CC2)O)C=2C=CC(OCCN3CCCC3)=CC=2)=CC=CC=C1 INEHJXCWEVNEDZ-LUDNRVPPSA-N 0.000 claims description 2
- UTYMHSHRSOOSEY-BYYHNAKLSA-N 4-[4-[(e)-2-chloro-1,2-diphenylethenyl]phenoxy]-n,n-diethylbutan-1-amine Chemical compound C1=CC(OCCCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 UTYMHSHRSOOSEY-BYYHNAKLSA-N 0.000 claims description 2
- ZQZFYGIXNQKOAV-OCEACIFDSA-N Droloxifene Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=C(O)C=CC=1)\C1=CC=C(OCCN(C)C)C=C1 ZQZFYGIXNQKOAV-OCEACIFDSA-N 0.000 claims description 2
- VWUXBMIQPBEWFH-WCCTWKNTSA-N Fulvestrant Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3[C@H](CCCCCCCCCS(=O)CCCC(F)(F)C(F)(F)F)CC2=C1 VWUXBMIQPBEWFH-WCCTWKNTSA-N 0.000 claims description 2
- JEYWNNAZDLFBFF-UHFFFAOYSA-N Nafoxidine Chemical compound C1CC2=CC(OC)=CC=C2C(C=2C=CC(OCCN3CCCC3)=CC=2)=C1C1=CC=CC=C1 JEYWNNAZDLFBFF-UHFFFAOYSA-N 0.000 claims description 2
- OEKMGABCSLYWOP-DHUJRADRSA-N [4-[(2s)-7-(2,2-dimethylpropanoyloxy)-4-methyl-2-[4-(2-piperidin-1-ylethoxy)phenyl]-2h-chromen-3-yl]phenyl] 2,2-dimethylpropanoate Chemical compound C1=CC([C@H]2C(=C(C3=CC=C(OC(=O)C(C)(C)C)C=C3O2)C)C=2C=CC(OC(=O)C(C)(C)C)=CC=2)=CC=C1OCCN1CCCCC1 OEKMGABCSLYWOP-DHUJRADRSA-N 0.000 claims description 2
- MCGDSOGUHLTADD-UHFFFAOYSA-N arzoxifene Chemical compound C1=CC(OC)=CC=C1C1=C(OC=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 MCGDSOGUHLTADD-UHFFFAOYSA-N 0.000 claims description 2
- 229950004203 droloxifene Drugs 0.000 claims description 2
- 229960002258 fulvestrant Drugs 0.000 claims description 2
- QZUHFMXJZOUZFI-ZQHSETAFSA-N miproxifene phosphate Chemical compound C=1C=C(C(C)C)C=CC=1C(/CC)=C(C=1C=CC(OP(O)(O)=O)=CC=1)\C1=CC=C(OCCN(C)C)C=C1 QZUHFMXJZOUZFI-ZQHSETAFSA-N 0.000 claims description 2
- 229950002366 nafoxidine Drugs 0.000 claims description 2
- 229960004622 raloxifene Drugs 0.000 claims description 2
- GZUITABIAKMVPG-UHFFFAOYSA-N raloxifene Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 GZUITABIAKMVPG-UHFFFAOYSA-N 0.000 claims description 2
- 229960005026 toremifene Drugs 0.000 claims description 2
- XFCLJVABOIYOMF-QPLCGJKRSA-N toremifene Chemical compound C1=CC(OCCN(C)C)=CC=C1C(\C=1C=CC=CC=1)=C(\CCCl)C1=CC=CC=C1 XFCLJVABOIYOMF-QPLCGJKRSA-N 0.000 claims description 2
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 2
- -1 1-[4-(2-azepan-1-yl-ethoxy)-benzyl]-2-(ethoxy-phenyl)-3-methyl-1H-indol-5-ol Chemical compound 0.000 claims 3
- LPDFEPVFKSNCDL-UHFFFAOYSA-N 3-chloro-2-(4-hydroxyphenyl)-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]indol-5-ol;hydrochloride Chemical compound Cl.C1=CC(O)=CC=C1C1=C(Cl)C2=CC(O)=CC=C2N1CC(C=C1)=CC=C1OCCN1CCCCC1 LPDFEPVFKSNCDL-UHFFFAOYSA-N 0.000 claims 2
- SZMIFQQICALUBG-UHFFFAOYSA-N [1-[[4-[2-(azepan-1-yl)ethoxy]phenyl]methyl]-2-(4-hydroxyphenyl)-3-methylindol-5-yl] acetate Chemical compound C=1C=C(O)C=CC=1C1=C(C)C2=CC(OC(=O)C)=CC=C2N1CC(C=C1)=CC=C1OCCN1CCCCCC1 SZMIFQQICALUBG-UHFFFAOYSA-N 0.000 claims 2
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 1
- NJPDBAAROZVZIV-UHFFFAOYSA-N 1-[[4-[2-(azepan-1-yl)ethoxy]phenyl]methyl]-2-(3-fluoro-4-hydroxyphenyl)-3-methylindol-5-ol Chemical compound C=1C=C(OCCN2CCCCCC2)C=CC=1CN1C2=CC=C(O)C=C2C(C)=C1C1=CC=C(O)C(F)=C1 NJPDBAAROZVZIV-UHFFFAOYSA-N 0.000 claims 1
- YHSACLNKCHFTRG-UHFFFAOYSA-N 1-[[4-[2-(azepan-1-yl)ethoxy]phenyl]methyl]-2-(3-fluoro-4-phenylmethoxyphenyl)-3-methyl-5-phenylmethoxyindole Chemical compound C=1C=C(OCCN2CCCCCC2)C=CC=1CN1C2=CC=C(OCC=3C=CC=CC=3)C=C2C(C)=C1C(C=C1F)=CC=C1OCC1=CC=CC=C1 YHSACLNKCHFTRG-UHFFFAOYSA-N 0.000 claims 1
- HLTXCZMYZMYHLI-UHFFFAOYSA-N 1-[[4-[2-(azepan-1-yl)ethoxy]phenyl]methyl]-2-(3-hydroxyphenyl)-3-methylindol-5-ol Chemical compound C=1C=C(OCCN2CCCCCC2)C=CC=1CN1C2=CC=C(O)C=C2C(C)=C1C1=CC=CC(O)=C1 HLTXCZMYZMYHLI-UHFFFAOYSA-N 0.000 claims 1
- IRKOQFZQDDXINL-UHFFFAOYSA-N 1-[[4-[2-(azepan-1-yl)ethoxy]phenyl]methyl]-2-(4-fluorophenyl)-3-methyl-5-phenylmethoxyindole Chemical compound C=1C=C(OCCN2CCCCCC2)C=CC=1CN1C2=CC=C(OCC=3C=CC=CC=3)C=C2C(C)=C1C1=CC=C(F)C=C1 IRKOQFZQDDXINL-UHFFFAOYSA-N 0.000 claims 1
- QMMNMFWQZAALAO-UHFFFAOYSA-N 1-[[4-[2-(azepan-1-yl)ethoxy]phenyl]methyl]-2-(4-fluorophenyl)-3-methylindol-5-ol Chemical compound C=1C=C(OCCN2CCCCCC2)C=CC=1CN1C2=CC=C(O)C=C2C(C)=C1C1=CC=C(F)C=C1 QMMNMFWQZAALAO-UHFFFAOYSA-N 0.000 claims 1
- COOWZQXURKSOKE-UHFFFAOYSA-N 1-[[4-[2-(azepan-1-yl)ethoxy]phenyl]methyl]-2-(4-hydroxyphenyl)-3-methylindol-5-ol;hydrochloride Chemical compound Cl.C=1C=C(OCCN2CCCCCC2)C=CC=1CN1C2=CC=C(O)C=C2C(C)=C1C1=CC=C(O)C=C1 COOWZQXURKSOKE-UHFFFAOYSA-N 0.000 claims 1
- ZFWOLILGCJYZAC-UHFFFAOYSA-N 1-[[4-[2-(azepan-1-yl)ethoxy]phenyl]methyl]-3-chloro-2-(4-hydroxyphenyl)indol-5-ol;hydrochloride Chemical compound Cl.C1=CC(O)=CC=C1C1=C(Cl)C2=CC(O)=CC=C2N1CC(C=C1)=CC=C1OCCN1CCCCCC1 ZFWOLILGCJYZAC-UHFFFAOYSA-N 0.000 claims 1
- VTNQNWHAPSXHQR-UHFFFAOYSA-N 1-[[4-[2-(azepan-1-yl)ethoxy]phenyl]methyl]-3-methyl-2-(4-propan-2-yloxyphenyl)indol-5-ol;hydrochloride Chemical compound Cl.C1=CC(OC(C)C)=CC=C1C1=C(C)C2=CC(O)=CC=C2N1CC(C=C1)=CC=C1OCCN1CCCCCC1 VTNQNWHAPSXHQR-UHFFFAOYSA-N 0.000 claims 1
- GLPVNLVSGIFUEL-UHFFFAOYSA-N 1-[[4-[2-(azepan-1-yl)ethoxy]phenyl]methyl]-3-methyl-2-phenyl-5-phenylmethoxyindole Chemical compound C=1C=C(OCCN2CCCCCC2)C=CC=1CN1C2=CC=C(OCC=3C=CC=CC=3)C=C2C(C)=C1C1=CC=CC=C1 GLPVNLVSGIFUEL-UHFFFAOYSA-N 0.000 claims 1
- ZKCVBEWOZNCCIY-UHFFFAOYSA-N 1-[[4-[2-(azepan-1-yl)ethoxy]phenyl]methyl]-3-methyl-2-phenylindol-5-ol;hydrochloride Chemical compound Cl.C=1C=C(OCCN2CCCCCC2)C=CC=1CN1C2=CC=C(O)C=C2C(C)=C1C1=CC=CC=C1 ZKCVBEWOZNCCIY-UHFFFAOYSA-N 0.000 claims 1
- JEWIDHWDWPLMEZ-UHFFFAOYSA-N 1-[[4-[2-(azepan-1-yl)ethoxy]phenyl]methyl]-3-methyl-5-phenylmethoxy-2-(3-phenylmethoxyphenyl)indole Chemical compound C=1C=C(OCCN2CCCCCC2)C=CC=1CN1C2=CC=C(OCC=3C=CC=CC=3)C=C2C(C)=C1C(C=1)=CC=CC=1OCC1=CC=CC=C1 JEWIDHWDWPLMEZ-UHFFFAOYSA-N 0.000 claims 1
- NXAHBBRIVLXMQA-UHFFFAOYSA-N 1-[[4-[2-(azepan-1-yl)ethoxy]phenyl]methyl]-3-methyl-5-phenylmethoxy-2-(4-phenylmethoxyphenyl)indole Chemical compound C=1C=C(OCCN2CCCCCC2)C=CC=1CN1C2=CC=C(OCC=3C=CC=CC=3)C=C2C(C)=C1C(C=C1)=CC=C1OCC1=CC=CC=C1 NXAHBBRIVLXMQA-UHFFFAOYSA-N 0.000 claims 1
- XPPGVEARJBKRJW-UHFFFAOYSA-N 1-[[4-[2-(azepan-1-yl)ethoxy]phenyl]methyl]-5-hydroxy-2-(4-hydroxyphenyl)indole-3-carbonitrile;hydrochloride Chemical compound Cl.C1=CC(O)=CC=C1C1=C(C#N)C2=CC(O)=CC=C2N1CC(C=C1)=CC=C1OCCN1CCCCCC1 XPPGVEARJBKRJW-UHFFFAOYSA-N 0.000 claims 1
- KCIWSFUGYXAPCY-UHFFFAOYSA-N 1-[[4-[2-(azepan-1-yl)ethoxy]phenyl]methyl]-5-methoxy-2-(4-methoxyphenyl)-3-methylindole;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C1=C(C)C2=CC(OC)=CC=C2N1CC(C=C1)=CC=C1OCCN1CCCCCC1 KCIWSFUGYXAPCY-UHFFFAOYSA-N 0.000 claims 1
- RLFBHJTVTVOEBB-UHFFFAOYSA-N 2-(2,4-dimethoxyphenyl)-3-methyl-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]indol-5-ol Chemical compound COC1=CC(OC)=CC=C1C1=C(C)C2=CC(O)=CC=C2N1CC(C=C1)=CC=C1OCCN1CCCCC1 RLFBHJTVTVOEBB-UHFFFAOYSA-N 0.000 claims 1
- DBIQTOWPZVCCTN-UHFFFAOYSA-N 2-(3-fluoro-4-hydroxyphenyl)-3-methyl-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]indol-5-ol Chemical compound C=1C=C(OCCN2CCCCC2)C=CC=1CN1C2=CC=C(O)C=C2C(C)=C1C1=CC=C(O)C(F)=C1 DBIQTOWPZVCCTN-UHFFFAOYSA-N 0.000 claims 1
- NWEKYYJYBYMBJM-UHFFFAOYSA-N 2-(3-fluoro-4-phenylmethoxyphenyl)-3-methyl-5-phenylmethoxy-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]indole Chemical compound C=1C=C(OCCN2CCCCC2)C=CC=1CN1C2=CC=C(OCC=3C=CC=CC=3)C=C2C(C)=C1C(C=C1F)=CC=C1OCC1=CC=CC=C1 NWEKYYJYBYMBJM-UHFFFAOYSA-N 0.000 claims 1
- GRNXCSPNKRKBIG-UHFFFAOYSA-N 2-(3-hydroxyphenyl)-3-methyl-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]indol-5-ol Chemical compound C=1C=C(OCCN2CCCCC2)C=CC=1CN1C2=CC=C(O)C=C2C(C)=C1C1=CC=CC(O)=C1 GRNXCSPNKRKBIG-UHFFFAOYSA-N 0.000 claims 1
- UONWVOBZHMOCFU-UHFFFAOYSA-N 2-(3-methoxyphenyl)-3-methyl-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]indol-5-ol Chemical compound COC1=CC=CC(C=2N(C3=CC=C(O)C=C3C=2C)CC=2C=CC(OCCN3CCCCC3)=CC=2)=C1 UONWVOBZHMOCFU-UHFFFAOYSA-N 0.000 claims 1
- MHYWHHQEOZHCIY-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-methyl-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]indol-5-ol;hydrochloride Chemical compound Cl.C=1C=C(OCCN2CCCCC2)C=CC=1CN1C2=CC=C(O)C=C2C(C)=C1C1=CC=C(Cl)C=C1 MHYWHHQEOZHCIY-UHFFFAOYSA-N 0.000 claims 1
- IEVRZEOVJVVBGY-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-methyl-5-phenylmethoxy-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]indole Chemical compound C=1C=C(OCCN2CCCCC2)C=CC=1CN1C2=CC=C(OCC=3C=CC=CC=3)C=C2C(C)=C1C1=CC=C(Cl)C=C1 IEVRZEOVJVVBGY-UHFFFAOYSA-N 0.000 claims 1
- BTDOAVCSLJTYJU-UHFFFAOYSA-N 2-(4-cyclopentyloxyphenyl)-3-methyl-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]indol-5-ol Chemical compound C=1C=C(OCCN2CCCCC2)C=CC=1CN1C2=CC=C(O)C=C2C(C)=C1C(C=C1)=CC=C1OC1CCCC1 BTDOAVCSLJTYJU-UHFFFAOYSA-N 0.000 claims 1
- CFBVBWXVYLXPJE-UHFFFAOYSA-N 2-(4-ethoxyphenyl)-3-methyl-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]indol-5-ol Chemical compound C1=CC(OCC)=CC=C1C1=C(C)C2=CC(O)=CC=C2N1CC(C=C1)=CC=C1OCCN1CCCCC1 CFBVBWXVYLXPJE-UHFFFAOYSA-N 0.000 claims 1
- LKLLLUUCQTWHTR-UHFFFAOYSA-N 2-(4-ethoxyphenyl)-3-methyl-5-phenylmethoxy-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]indole Chemical compound C1=CC(OCC)=CC=C1C1=C(C)C2=CC(OCC=3C=CC=CC=3)=CC=C2N1CC(C=C1)=CC=C1OCCN1CCCCC1 LKLLLUUCQTWHTR-UHFFFAOYSA-N 0.000 claims 1
- RRPDMZIDZGKVEZ-UHFFFAOYSA-N 2-(4-fluorophenyl)-3-methyl-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]indol-5-ol;hydrochloride Chemical compound Cl.C=1C=C(OCCN2CCCCC2)C=CC=1CN1C2=CC=C(O)C=C2C(C)=C1C1=CC=C(F)C=C1 RRPDMZIDZGKVEZ-UHFFFAOYSA-N 0.000 claims 1
- BXDCWPQERLZULN-UHFFFAOYSA-N 2-(4-fluorophenyl)-3-methyl-5-phenylmethoxy-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]indole Chemical compound C=1C=C(OCCN2CCCCC2)C=CC=1CN1C2=CC=C(OCC=3C=CC=CC=3)C=C2C(C)=C1C1=CC=C(F)C=C1 BXDCWPQERLZULN-UHFFFAOYSA-N 0.000 claims 1
- SDIHKMFKQGSAJU-UHFFFAOYSA-N 2-(4-hydroxy-3-methoxyphenyl)-3-methyl-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]indol-5-ol;hydrochloride Chemical compound Cl.C1=C(O)C(OC)=CC(C=2N(C3=CC=C(O)C=C3C=2C)CC=2C=CC(OCCN3CCCCC3)=CC=2)=C1 SDIHKMFKQGSAJU-UHFFFAOYSA-N 0.000 claims 1
- JICOGKJOQXTAIP-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-3-methyl-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]indol-5-ol Chemical compound C=1C=C(OCCN2CCCCC2)C=CC=1CN1C2=CC=C(O)C=C2C(C)=C1C1=CC=C(O)C=C1 JICOGKJOQXTAIP-UHFFFAOYSA-N 0.000 claims 1
- VBEXJFYMTIILAI-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-3-methyl-1-[[4-(2-pyrrolidin-1-ylethoxy)phenyl]methyl]indol-5-ol Chemical compound C=1C=C(OCCN2CCCC2)C=CC=1CN1C2=CC=C(O)C=C2C(C)=C1C1=CC=C(O)C=C1 VBEXJFYMTIILAI-UHFFFAOYSA-N 0.000 claims 1
- QFGIIRQJHPVWMH-UHFFFAOYSA-N 3-chloro-2-(4-hydroxy-2-methylphenyl)-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]indol-5-ol Chemical compound CC1=CC(O)=CC=C1C1=C(Cl)C2=CC(O)=CC=C2N1CC(C=C1)=CC=C1OCCN1CCCCC1 QFGIIRQJHPVWMH-UHFFFAOYSA-N 0.000 claims 1
- KWZKQKHDVUIZMJ-UHFFFAOYSA-N 3-ethyl-2-(4-hydroxyphenyl)-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]indol-5-ol;hydrochloride Chemical compound Cl.C=1C=C(OCCN2CCCCC2)C=CC=1CN1C2=CC=C(O)C=C2C(CC)=C1C1=CC=C(O)C=C1 KWZKQKHDVUIZMJ-UHFFFAOYSA-N 0.000 claims 1
- VSEWKHFOOMLOKE-UHFFFAOYSA-N 3-methyl-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]-2-(4-propan-2-yloxyphenyl)indol-5-ol;hydrochloride Chemical compound Cl.C1=CC(OC(C)C)=CC=C1C1=C(C)C2=CC(O)=CC=C2N1CC(C=C1)=CC=C1OCCN1CCCCC1 VSEWKHFOOMLOKE-UHFFFAOYSA-N 0.000 claims 1
- DJMHECLYFXQQCT-UHFFFAOYSA-N 3-methyl-2-(4-methylphenyl)-5-phenylmethoxy-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]indole Chemical compound C=1C=C(OCCN2CCCCC2)C=CC=1CN1C2=CC=C(OCC=3C=CC=CC=3)C=C2C(C)=C1C1=CC=C(C)C=C1 DJMHECLYFXQQCT-UHFFFAOYSA-N 0.000 claims 1
- CNZIGHBGAPKVTE-UHFFFAOYSA-N 3-methyl-2-phenyl-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]indol-5-ol;hydrochloride Chemical compound Cl.C=1C=C(OCCN2CCCCC2)C=CC=1CN1C2=CC=C(O)C=C2C(C)=C1C1=CC=CC=C1 CNZIGHBGAPKVTE-UHFFFAOYSA-N 0.000 claims 1
- IPPCWZMRTPZJGB-UHFFFAOYSA-N 3-methyl-5-phenylmethoxy-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]-2-(4-propan-2-yloxyphenyl)indole Chemical compound C1=CC(OC(C)C)=CC=C1C1=C(C)C2=CC(OCC=3C=CC=CC=3)=CC=C2N1CC(C=C1)=CC=C1OCCN1CCCCC1 IPPCWZMRTPZJGB-UHFFFAOYSA-N 0.000 claims 1
- ORULONJLCMMVET-UHFFFAOYSA-N 3-methyl-5-phenylmethoxy-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]-2-[4-(trifluoromethoxy)phenyl]indole Chemical compound C=1C=C(OCCN2CCCCC2)C=CC=1CN1C2=CC=C(OCC=3C=CC=CC=3)C=C2C(C)=C1C1=CC=C(OC(F)(F)F)C=C1 ORULONJLCMMVET-UHFFFAOYSA-N 0.000 claims 1
- ATXFFPXTECEUDK-UHFFFAOYSA-N 3-methyl-5-phenylmethoxy-2-(3-phenylmethoxyphenyl)-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]indole Chemical compound C=1C=C(OCCN2CCCCC2)C=CC=1CN1C2=CC=C(OCC=3C=CC=CC=3)C=C2C(C)=C1C(C=1)=CC=CC=1OCC1=CC=CC=C1 ATXFFPXTECEUDK-UHFFFAOYSA-N 0.000 claims 1
- FUUJGUSPAXKNFK-UHFFFAOYSA-N 3-methyl-5-phenylmethoxy-2-(4-phenylmethoxyphenyl)-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]indole Chemical compound C=1C=C(OCCN2CCCCC2)C=CC=1CN1C2=CC=C(OCC=3C=CC=CC=3)C=C2C(C)=C1C(C=C1)=CC=C1OCC1=CC=CC=C1 FUUJGUSPAXKNFK-UHFFFAOYSA-N 0.000 claims 1
- YIKXUOSESRXTQN-UHFFFAOYSA-N 4-[5-fluoro-3-methyl-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]indol-2-yl]phenol;hydrochloride Chemical compound Cl.C=1C=C(OCCN2CCCCC2)C=CC=1CN1C2=CC=C(F)C=C2C(C)=C1C1=CC=C(O)C=C1 YIKXUOSESRXTQN-UHFFFAOYSA-N 0.000 claims 1
- KLLQIDUWMBJRFJ-UHFFFAOYSA-N 5-hydroxy-2-(4-hydroxyphenyl)-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]indole-3-carbonitrile;hydrochloride Chemical compound Cl.C1=CC(O)=CC=C1C1=C(C#N)C2=CC(O)=CC=C2N1CC(C=C1)=CC=C1OCCN1CCCCC1 KLLQIDUWMBJRFJ-UHFFFAOYSA-N 0.000 claims 1
- DBSJTXLRFCVLGH-UHFFFAOYSA-N 5-methoxy-2-(4-methoxyphenyl)-3-methyl-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]indole;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C1=C(C)C2=CC(OC)=CC=C2N1CC(C=C1)=CC=C1OCCN1CCCCC1 DBSJTXLRFCVLGH-UHFFFAOYSA-N 0.000 claims 1
- DTWMLAXIQKMJLG-UHFFFAOYSA-N C(CC)(=O)O.C(CC)(=O)O.Cl.N1(CCCCCC1)CCOC1=CC=C(CN2C(=C(C3=CC(=CC=C23)O)C)C2=CC=C(C=C2)O)C=C1 Chemical compound C(CC)(=O)O.C(CC)(=O)O.Cl.N1(CCCCCC1)CCOC1=CC=C(CN2C(=C(C3=CC(=CC=C23)O)C)C2=CC=C(C=C2)O)C=C1 DTWMLAXIQKMJLG-UHFFFAOYSA-N 0.000 claims 1
- KSTVZKRXKAOTAV-UHFFFAOYSA-N Cl.C(C(C)(C)C)(=O)O.C(C(C)(C)C)(=O)O.N1(CCCCCC1)CCOC1=CC=C(CN2C(=C(C3=CC(=CC=C23)O)C)C2=CC=C(C=C2)O)C=C1 Chemical compound Cl.C(C(C)(C)C)(=O)O.C(C(C)(C)C)(=O)O.N1(CCCCCC1)CCOC1=CC=C(CN2C(=C(C3=CC(=CC=C23)O)C)C2=CC=C(C=C2)O)C=C1 KSTVZKRXKAOTAV-UHFFFAOYSA-N 0.000 claims 1
- JJKOTMDDZAJTGQ-DQSJHHFOSA-N Idoxifene Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN2CCCC2)=CC=1)/C1=CC=C(I)C=C1 JJKOTMDDZAJTGQ-DQSJHHFOSA-N 0.000 claims 1
- UCJGJABZCDBEDK-UHFFFAOYSA-N bazedoxifene Chemical compound C=1C=C(OCCN2CCCCCC2)C=CC=1CN1C2=CC=C(O)C=C2C(C)=C1C1=CC=C(O)C=C1 UCJGJABZCDBEDK-UHFFFAOYSA-N 0.000 claims 1
- 229950002248 idoxifene Drugs 0.000 claims 1
- 229950010765 pivalate Drugs 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- 230000002354 daily effect Effects 0.000 description 9
- 150000003146 progesterones Chemical class 0.000 description 4
- 208000032843 Hemorrhage Diseases 0.000 description 3
- 230000000740 bleeding effect Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229940124558 contraceptive agent Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 210000004696 endometrium Anatomy 0.000 description 3
- 206010046788 Uterine haemorrhage Diseases 0.000 description 2
- 206010046910 Vaginal haemorrhage Diseases 0.000 description 2
- 210000003756 cervix mucus Anatomy 0.000 description 2
- 230000003203 everyday effect Effects 0.000 description 2
- 230000001788 irregular Effects 0.000 description 2
- 230000016087 ovulation Effects 0.000 description 2
- 230000035935 pregnancy Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229940077150 progesterone and estrogen Drugs 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- 102000006771 Gonadotropins Human genes 0.000 description 1
- 108010086677 Gonadotropins Proteins 0.000 description 1
- 206010027514 Metrorrhagia Diseases 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002513 anti-ovulatory effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000002051 biphasic effect Effects 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
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000002357 endometrial effect Effects 0.000 description 1
- 230000001076 estrogenic effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 239000002622 gonadotropin Substances 0.000 description 1
- 229940094892 gonadotropins Drugs 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000002513 implantation 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
- 230000005906 menstruation Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229940068196 placebo Drugs 0.000 description 1
- 239000000902 placebo Substances 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
- 239000000126 substance Substances 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Gynecology & Obstetrics (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US96508397A | 1997-11-06 | 1997-11-06 | |
| PCT/US1998/023427 WO1999024027A2 (en) | 1997-11-06 | 1998-11-04 | Anti-estrogen plus progestin containing oral contraceptives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20000269A2 true HRP20000269A2 (en) | 2000-12-31 |
Family
ID=25509417
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20000269A HRP20000269A2 (en) | 1997-11-06 | 2000-05-05 | Anti-estrogen plus progestin containing oral contraceptives |
Country Status (28)
| Country | Link |
|---|---|
| EP (1) | EP1051179B1 (pt) |
| JP (1) | JP2001522798A (pt) |
| CN (1) | CN1278732A (pt) |
| AR (1) | AR016667A1 (pt) |
| AT (1) | ATE304359T1 (pt) |
| AU (2) | AU760540B2 (pt) |
| BG (1) | BG104451A (pt) |
| BR (1) | BR9813982A (pt) |
| CA (1) | CA2307210A1 (pt) |
| CZ (1) | CZ294155B6 (pt) |
| DE (1) | DE69831605T2 (pt) |
| DK (1) | DK1051179T3 (pt) |
| EA (1) | EA200000492A1 (pt) |
| EE (1) | EE04092B1 (pt) |
| ES (1) | ES2246541T3 (pt) |
| GE (1) | GEP20043290B (pt) |
| HR (1) | HRP20000269A2 (pt) |
| HU (1) | HUP0100293A3 (pt) |
| ID (1) | ID24568A (pt) |
| IL (1) | IL135621A0 (pt) |
| NO (1) | NO20002167L (pt) |
| NZ (1) | NZ503890A (pt) |
| PL (1) | PL340623A1 (pt) |
| SK (1) | SK6482000A3 (pt) |
| TR (1) | TR200001268T2 (pt) |
| UA (1) | UA68365C2 (pt) |
| WO (1) | WO1999024027A2 (pt) |
| ZA (1) | ZA9810136B (pt) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL120263A0 (en) * | 1996-02-28 | 1997-06-10 | Pfizer | Combination therapy to prevent bone loss-progesterone and estrogen agonists |
| US6479535B1 (en) | 1998-05-15 | 2002-11-12 | Wyeth | 2-phenyl-1-[4-(2-aminoethoxy)-benzyl]-indole and estrogen formulations |
| BR9911040A (pt) * | 1998-05-15 | 2001-02-13 | American Home Prod | 2-fenil-1-[4-(2-aminoetóxi)-benzil]-indol em combinação com estrogêneos |
| US6380166B1 (en) | 1999-09-13 | 2002-04-30 | American Home Products Corporation | Glucopyranosides conjugates of 2-(4-hydroxy-phenyl)-3-methyl-1-[4-(2-amin-1-yl-ethoxy)-benzyl]-1H-indol-5-ols |
| WO2001019839A1 (en) * | 1999-09-13 | 2001-03-22 | American Home Products Corporation | Glucopyranosides conjugates of 2-(4-hydroxy-phenyl)-1-[4-(2-amin-1-yl-ethoxy)-benzyl]-1h-indol-5-ols |
| US6376486B1 (en) | 2000-07-06 | 2002-04-23 | American Home Products Corporation | Methods of inhibiting sphincter incontinence |
| CN1599606A (zh) | 2001-07-31 | 2005-03-23 | 辉瑞产品公司 | 包含雌激素激动剂/拮抗剂、雌激素与孕激素组合的药物组合物、试剂盒和方法 |
| WO2006049889A1 (en) | 2004-10-27 | 2006-05-11 | Janssen Pharmaceutica N.V. | Indole derivatives useful as progesterone receptor modulators |
| FR2880625B1 (fr) * | 2005-01-07 | 2007-03-09 | Sanofi Aventis Sa | Derives de n-(heteroaryl)-1h-indole-2-carboxamides, leur preparation et leur application en therapeutique |
| UY29527A1 (es) * | 2005-05-13 | 2006-12-29 | Schering Ag | Composicinn farmaccutica que contienen gestrgenos y/o estrngenos y 5-metil - (6s) - tetrhidrofolato. |
| DE102008057230A1 (de) * | 2008-11-11 | 2010-05-12 | Bayer Schering Pharma Aktiengesellschaft | Synergistische pharmazeutische Kombination mit einem Estrogenrezeptorantagonisten und einem Progestin |
| RS56042B1 (sr) | 2010-06-10 | 2017-09-29 | Seragon Pharmaceuticals Inc | Modulatori estrogenih receptora i njihove upotrebe |
| US9193714B2 (en) | 2011-12-14 | 2015-11-24 | Seragon Pharmaceuticals, Inc. | Fluorinated estrogen receptor modulators and uses thereof |
| AU2016331065B2 (en) | 2015-10-01 | 2021-04-29 | Olema Pharmaceuticals, Inc. | Tetrahydro-1H-pyrido(3,4-b)indole anti-estrogenic drugs |
| AU2016366680B2 (en) | 2015-12-09 | 2021-06-24 | The Board Of Trustees Of The University Of Illinois | Benzothiophene-based selective estrogen receptor downregulators |
| WO2017197036A1 (en) | 2016-05-10 | 2017-11-16 | C4 Therapeutics, Inc. | Spirocyclic degronimers for target protein degradation |
| CN109562107A (zh) | 2016-05-10 | 2019-04-02 | C4医药公司 | 用于靶蛋白降解的杂环降解决定子体 |
| CN109641874A (zh) | 2016-05-10 | 2019-04-16 | C4医药公司 | 用于靶蛋白降解的c3-碳连接的戊二酰亚胺降解决定子体 |
| RU2019102647A (ru) | 2016-07-01 | 2020-08-03 | Г1 Терапьютикс, Инк. | Антипролиферационные средства на основе пиримидина |
| WO2018081168A2 (en) | 2016-10-24 | 2018-05-03 | The Board Of Trustees Of The University Of Illinois | Benzothiophene-based selective mixed estrogen receptor downregulators |
| IL267795B2 (en) | 2017-01-06 | 2023-02-01 | G1 Therapeutics Inc | Combined treatment for cancer |
| JP2020507566A (ja) | 2017-02-10 | 2020-03-12 | ジー１ セラピューティクス， インコーポレイテッド | ベンゾチオフェンエストロゲン受容体モジュレーター |
| AU2018291026B2 (en) | 2017-06-29 | 2022-09-01 | G1 Therapeutics, Inc. | Morphic forms of GIT38 and methods of manufacture thereof |
| WO2020132561A1 (en) | 2018-12-20 | 2020-06-25 | C4 Therapeutics, Inc. | Targeted protein degradation |
| BR112022011827A2 (pt) | 2019-12-20 | 2022-08-30 | C4 Therapeutics Inc | Composto, composição farmacêutica, uso de um composto, métodos para tratamento ou profilaxia de câncer e para tratar um paciente com um distúrbio mediado por receptor do fator de crescimento epidérmico, e, invenção |
| WO2024030968A1 (en) | 2022-08-03 | 2024-02-08 | Brystol-Myers Squibb Company | Compounds for modulating ret protein |
| WO2024097989A1 (en) | 2022-11-04 | 2024-05-10 | Bristol-Myers Squibb Company | Ret-ldd protein degraders |
| WO2024097980A1 (en) | 2022-11-04 | 2024-05-10 | Bristol-Myers Squibb Company | Ret-ldd protein inhibitors |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA716118B (en) * | 1970-10-05 | 1972-05-31 | Richardson Merrell Inc | Contraception |
| ZA9510926B (en) * | 1994-12-23 | 1996-07-03 | Schering Ag | Compounds with progesterone-antagonistic and antiestrogenic action to be used together for female contraception |
| IL120263A0 (en) * | 1996-02-28 | 1997-06-10 | Pfizer | Combination therapy to prevent bone loss-progesterone and estrogen agonists |
| IL120266A (en) * | 1996-02-28 | 2005-05-17 | Pfizer | Use of estrogen antagonists and estrogen agonists in the preparation of medicaments for inhibiting pathological conditions |
| SK281737B6 (sk) * | 1996-04-19 | 2001-07-10 | American Home Products Corporation | 2-fenylindolové zlúčeniny, farmaceutický prostriedok s ich obsahom a ich použitie |
| US5747480A (en) * | 1996-05-08 | 1998-05-05 | American Home Products Corporation | Oral contraceptive |
-
1998
- 1998-04-11 UA UA2000063196A patent/UA68365C2/uk unknown
- 1998-04-11 ID IDW20000811A patent/ID24568A/id unknown
- 1998-11-04 DE DE69831605T patent/DE69831605T2/de not_active Expired - Lifetime
- 1998-11-04 EE EEP200000211A patent/EE04092B1/xx not_active IP Right Cessation
- 1998-11-04 IL IL13562198A patent/IL135621A0/xx unknown
- 1998-11-04 AU AU13031/99A patent/AU760540B2/en not_active Ceased
- 1998-11-04 DK DK98956525T patent/DK1051179T3/da active
- 1998-11-04 HU HU0100293A patent/HUP0100293A3/hu unknown
- 1998-11-04 BR BR9813982-7A patent/BR9813982A/pt not_active Application Discontinuation
- 1998-11-04 JP JP2000520119A patent/JP2001522798A/ja not_active Ceased
- 1998-11-04 AT AT98956525T patent/ATE304359T1/de not_active IP Right Cessation
- 1998-11-04 CN CN98810911A patent/CN1278732A/zh active Pending
- 1998-11-04 CA CA002307210A patent/CA2307210A1/en not_active Abandoned
- 1998-11-04 NZ NZ503890A patent/NZ503890A/xx unknown
- 1998-11-04 SK SK648-2000A patent/SK6482000A3/sk unknown
- 1998-11-04 EP EP98956525A patent/EP1051179B1/en not_active Expired - Lifetime
- 1998-11-04 CZ CZ20001661A patent/CZ294155B6/cs not_active IP Right Cessation
- 1998-11-04 PL PL98340623A patent/PL340623A1/xx unknown
- 1998-11-04 TR TR2000/01268T patent/TR200001268T2/xx unknown
- 1998-11-04 ES ES98956525T patent/ES2246541T3/es not_active Expired - Lifetime
- 1998-11-04 WO PCT/US1998/023427 patent/WO1999024027A2/en not_active Application Discontinuation
- 1998-11-04 EA EA200000492A patent/EA200000492A1/ru unknown
- 1998-11-04 GE GEAP19985364A patent/GEP20043290B/en unknown
- 1998-11-05 AR ARP980105591A patent/AR016667A1/es not_active Application Discontinuation
- 1998-11-05 ZA ZA9810136A patent/ZA9810136B/xx unknown
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2000
- 2000-04-27 NO NO20002167A patent/NO20002167L/no not_active Application Discontinuation
- 2000-05-05 HR HR20000269A patent/HRP20000269A2/hr not_active Application Discontinuation
- 2000-05-17 BG BG104451A patent/BG104451A/xx unknown
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2003
- 2003-06-23 AU AU2003204896A patent/AU2003204896B2/en not_active Ceased
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