KR100480193B1 - 에스트로겐제제및이를포함하는약제학적조성물 - Google Patents

Info

Publication number

KR100480193B1

KR100480193B1 KR1019970014894A KR19970014894A KR100480193B1 KR 100480193 B1 KR100480193 B1 KR 100480193B1 KR 1019970014894 A KR1019970014894 A KR 1019970014894A KR 19970014894 A KR19970014894 A KR 19970014894A KR 100480193 B1 KR100480193 B1 KR 100480193B1

Authority

KR

South Korea

Prior art keywords

compound

phenyl

methyl

benzyl

ethoxy

Prior art date

1996-04-19

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Lifetime

Links

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• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 8
• 239000000262 estrogen Substances 0.000 title abstract description 27
• 229940011871 estrogen Drugs 0.000 title abstract description 27
• 238000002360 preparation method Methods 0.000 title abstract description 7
• 150000001875 compounds Chemical class 0.000 claims abstract description 241
• 238000011282 treatment Methods 0.000 claims abstract description 28
• -1 C 1 -C 4 alkoxy Chemical group 0.000 claims description 121
• 150000003839 salts Chemical class 0.000 claims description 92
• SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 62
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 39
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 39
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 25
• 229910052739 hydrogen Inorganic materials 0.000 claims description 24
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 22
• 229910052736 halogen Inorganic materials 0.000 claims description 18
• 150000002367 halogens Chemical class 0.000 claims description 18
• 125000003282 alkyl amino group Chemical group 0.000 claims description 17
• 239000001257 hydrogen Substances 0.000 claims description 15
• 125000001424 substituent group Chemical group 0.000 claims description 14
• 125000004953 trihalomethyl group Chemical group 0.000 claims description 13
• 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 12
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 12
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
• 125000004951 trihalomethoxy group Chemical group 0.000 claims description 12
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 11
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
• 229910052799 carbon Inorganic materials 0.000 claims description 10
• 201000010099 disease Diseases 0.000 claims description 10
• 150000002148 esters Chemical class 0.000 claims description 10
• 150000005215 alkyl ethers Chemical class 0.000 claims description 9
• 150000002475 indoles Chemical class 0.000 claims description 9
• LMIQERWZRIFWNZ-UHFFFAOYSA-N 5-hydroxyindole Chemical compound OC1=CC=C2NC=CC2=C1 LMIQERWZRIFWNZ-UHFFFAOYSA-N 0.000 claims description 7
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
• MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
• 206010065687 Bone loss Diseases 0.000 claims description 4
• 206010014733 Endometrial cancer Diseases 0.000 claims description 4
• 206010014759 Endometrial neoplasm Diseases 0.000 claims description 4
• 125000004122 cyclic group Chemical group 0.000 claims description 4
• 125000001041 indolyl group Chemical group 0.000 claims description 4
• SMYMDRJWEFCCCI-UHFFFAOYSA-N trichloro(trichloromethoxy)methane Chemical compound ClC(Cl)(Cl)OC(Cl)(Cl)Cl SMYMDRJWEFCCCI-UHFFFAOYSA-N 0.000 claims description 4
• WZEOZJQLTRFNCU-UHFFFAOYSA-N trifluoro(trifluoromethoxy)methane Chemical compound FC(F)(F)OC(F)(F)F WZEOZJQLTRFNCU-UHFFFAOYSA-N 0.000 claims description 4
• 208000026310 Breast neoplasm Diseases 0.000 claims description 3
• 159000000021 acetate salts Chemical group 0.000 claims description 3
• 239000003814 drug Substances 0.000 claims description 3
• 230000002357 endometrial effect Effects 0.000 claims description 3
• QICKWGKIIULNMB-UHFFFAOYSA-N 1-[[4-[2-(dibutylamino)ethoxy]phenyl]methyl]-2-(4-hydroxyphenyl)-3-methylindol-5-ol Chemical compound C1=CC(OCCN(CCCC)CCCC)=CC=C1CN1C2=CC=C(O)C=C2C(C)=C1C1=CC=C(O)C=C1 QICKWGKIIULNMB-UHFFFAOYSA-N 0.000 claims description 2
• IWOGIWNWSAFOMC-UHFFFAOYSA-N 1-[[4-[2-(dipropylamino)ethoxy]phenyl]methyl]-2-(4-hydroxyphenyl)-3-methylindol-5-ol Chemical compound C1=CC(OCCN(CCC)CCC)=CC=C1CN1C2=CC=C(O)C=C2C(C)=C1C1=CC=C(O)C=C1 IWOGIWNWSAFOMC-UHFFFAOYSA-N 0.000 claims description 2
• SNCLWYBESLKSRY-VWNXMTODSA-N 1-[[4-[2-[(1r,4s)-3-azabicyclo[2.2.1]heptan-3-yl]ethoxy]phenyl]methyl]-2-(4-hydroxyphenyl)-3-methylindol-5-ol Chemical compound N1([C@@]2([H])CC[C@](C2)(C1)[H])CCOC(C=C1)=CC=C1CN(C1=CC=C(O)C=C1C=1C)C=1C1=CC=C(O)C=C1 SNCLWYBESLKSRY-VWNXMTODSA-N 0.000 claims description 2
• WANIEUSUVJHWKZ-SZPZYZBQSA-N 1-[[4-[2-[(2s,6r)-2,6-dimethylpiperidin-1-yl]ethoxy]phenyl]methyl]-2-(4-hydroxyphenyl)-3-methylindol-5-ol Chemical compound C[C@H]1CCC[C@@H](C)N1CCOC(C=C1)=CC=C1CN1C2=CC=C(O)C=C2C(C)=C1C1=CC=C(O)C=C1 WANIEUSUVJHWKZ-SZPZYZBQSA-N 0.000 claims description 2
• JJGBHIULHLZNIW-UHFFFAOYSA-N 1-[[4-[2-[di(propan-2-yl)amino]ethoxy]phenyl]methyl]-2-(4-hydroxyphenyl)-3-methylindol-5-ol Chemical compound C1=CC(OCCN(C(C)C)C(C)C)=CC=C1CN1C2=CC=C(O)C=C2C(C)=C1C1=CC=C(O)C=C1 JJGBHIULHLZNIW-UHFFFAOYSA-N 0.000 claims description 2
• XNGTUCXVYKSSHF-UHFFFAOYSA-N 2-(4-chlorophenyl)-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(Cl)C=C1 XNGTUCXVYKSSHF-UHFFFAOYSA-N 0.000 claims description 2
• LKLLLUUCQTWHTR-UHFFFAOYSA-N 2-(4-ethoxyphenyl)-3-methyl-5-phenylmethoxy-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]indole Chemical class 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 description 2
• BXDCWPQERLZULN-UHFFFAOYSA-N 2-(4-fluorophenyl)-3-methyl-5-phenylmethoxy-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]indole Chemical class 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 description 2
• YQJWJOBDSRSRFN-UHFFFAOYSA-N 2-(4-hydroxy-3-methoxyphenyl)-3-methyl-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]indol-5-ol Chemical compound C1=C(O)C(OC)=CC(C=2N(C3=CC=C(O)C=C3C=2C)CC=2C=CC(OCCN3CCCCC3)=CC=2)=C1 YQJWJOBDSRSRFN-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• CPFQIGOYNWIBFK-UHFFFAOYSA-N 3-chloro-5-phenylmethoxy-2-(4-phenylmethoxyphenyl)-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]indole Chemical class C=1C=C(OCCN2CCCCC2)C=CC=1CN1C2=CC=C(OCC=3C=CC=CC=3)C=C2C(Cl)=C1C(C=C1)=CC=C1OCC1=CC=CC=C1 CPFQIGOYNWIBFK-UHFFFAOYSA-N 0.000 claims description 2
• QTNPDFDSYCWELQ-UHFFFAOYSA-N 3-ethyl-5-phenylmethoxy-2-(4-phenylmethoxyphenyl)-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]indole Chemical class C=1C=C(OCCN2CCCCC2)C=CC=1CN1C2=CC=C(OCC=3C=CC=CC=3)C=C2C(CC)=C1C(C=C1)=CC=C1OCC1=CC=CC=C1 QTNPDFDSYCWELQ-UHFFFAOYSA-N 0.000 claims description 2
• BQYMNRMHTXRMGR-UHFFFAOYSA-N 3-methyl-2-phenyl-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=C1 BQYMNRMHTXRMGR-UHFFFAOYSA-N 0.000 claims description 2
• ATXFFPXTECEUDK-UHFFFAOYSA-N 3-methyl-5-phenylmethoxy-2-(3-phenylmethoxyphenyl)-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]indole Chemical class 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 description 2
• FUUJGUSPAXKNFK-UHFFFAOYSA-N 3-methyl-5-phenylmethoxy-2-(4-phenylmethoxyphenyl)-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]indole Chemical class 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 description 2
• FBCLHHRZKNDZAZ-UHFFFAOYSA-N 3-methyl-5-phenylmethoxy-2-(4-phenylmethoxyphenyl)-1-[[4-(3-piperidin-1-ylpropoxy)phenyl]methyl]indole Chemical class C=1C=C(OCCCN2CCCCC2)C=CC=1CN1C2=CC=C(OCC=3C=CC=CC=3)C=C2C(C)=C1C(C=C1)=CC=C1OCC1=CC=CC=C1 FBCLHHRZKNDZAZ-UHFFFAOYSA-N 0.000 claims description 2
• IPCBICMFFHDIIG-UHFFFAOYSA-N 4-[5-fluoro-3-methyl-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]indol-2-yl]phenol Chemical compound C=1C=C(OCCN2CCCCC2)C=CC=1CN1C2=CC=C(F)C=C2C(C)=C1C1=CC=C(O)C=C1 IPCBICMFFHDIIG-UHFFFAOYSA-N 0.000 claims description 2
• CKXCJRUGPCPEMZ-UHFFFAOYSA-N 4-[5-methoxy-3-methyl-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]indol-2-yl]phenol Chemical compound C=1C=C(O)C=CC=1C1=C(C)C2=CC(OC)=CC=C2N1CC(C=C1)=CC=C1OCCN1CCCCC1 CKXCJRUGPCPEMZ-UHFFFAOYSA-N 0.000 claims description 2
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
• 208000002874 Acne Vulgaris Diseases 0.000 claims description 2
• 201000004384 Alopecia Diseases 0.000 claims description 2
• 208000024827 Alzheimer disease Diseases 0.000 claims description 2
• 206010003694 Atrophy Diseases 0.000 claims description 2
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 2
• 206010009944 Colon cancer Diseases 0.000 claims description 2
• 206010013908 Dysfunctional uterine bleeding Diseases 0.000 claims description 2
• 206010027514 Metrorrhagia Diseases 0.000 claims description 2
• 206010060862 Prostate cancer Diseases 0.000 claims description 2
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 2
• 208000015815 Rectal disease Diseases 0.000 claims description 2
• 206010000496 acne Diseases 0.000 claims description 2
• 230000037444 atrophy Effects 0.000 claims description 2
• 201000007455 central nervous system cancer Diseases 0.000 claims description 2
• 208000015114 central nervous system disease Diseases 0.000 claims description 2
• 230000001684 chronic effect Effects 0.000 claims description 2
• 208000029742 colonic neoplasm Diseases 0.000 claims description 2
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• 230000003676 hair loss Effects 0.000 claims description 2
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• 208000019423 liver disease Diseases 0.000 claims description 2
• 201000001441 melanoma Diseases 0.000 claims description 2
• 201000010065 polycystic ovary syndrome Diseases 0.000 claims description 2
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• 206010046811 uterine polyp Diseases 0.000 claims description 2
• 230000002087 whitening effect Effects 0.000 claims description 2
• 125000001475 halogen functional group Chemical group 0.000 claims 6
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 6
• 125000000217 alkyl group Chemical group 0.000 claims 4
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 3
• ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical group C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims 3
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 2
• NPZACNAERPDSGY-UHFFFAOYSA-N 1-[[4-[2-(azocan-1-yl)ethoxy]phenyl]methyl]-2-(4-hydroxyphenyl)-3-methylindol-5-ol Chemical compound C=1C=C(OCCN2CCCCCCC2)C=CC=1CN1C2=CC=C(O)C=C2C(C)=C1C1=CC=C(O)C=C1 NPZACNAERPDSGY-UHFFFAOYSA-N 0.000 claims 1
• FNNWTXMUBMHNOD-UHFFFAOYSA-N 1-methylindol-5-ol Chemical group OC1=CC=C2N(C)C=CC2=C1 FNNWTXMUBMHNOD-UHFFFAOYSA-N 0.000 claims 1
• IRJAERPTWHZZOI-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-3-methyl-1-[[4-[2-(4-methylpiperidin-1-yl)ethoxy]phenyl]methyl]indol-5-ol Chemical compound C1CC(C)CCN1CCOC(C=C1)=CC=C1CN1C2=CC=C(O)C=C2C(C)=C1C1=CC=C(O)C=C1 IRJAERPTWHZZOI-UHFFFAOYSA-N 0.000 claims 1
• 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 1
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
• UWLYKIFSJQWOHY-UHFFFAOYSA-N 3-methyl-2-(4-methylphenyl)-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(C)C=C1 UWLYKIFSJQWOHY-UHFFFAOYSA-N 0.000 claims 1
• FUFZNHHSSMCXCZ-UHFFFAOYSA-N 5-piperidin-4-yl-3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazole Chemical group FC(F)(F)C1=CC=CC(C=2N=C(ON=2)C2CCNCC2)=C1 FUFZNHHSSMCXCZ-UHFFFAOYSA-N 0.000 claims 1
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• 235000001484 Trigonella foenum graecum Nutrition 0.000 claims 1
• 244000250129 Trigonella foenum graecum Species 0.000 claims 1
• 230000006999 cognitive decline Effects 0.000 claims 1
• 208000010877 cognitive disease Diseases 0.000 claims 1
• GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 1
• 150000004704 methoxides Chemical class 0.000 claims 1
• 125000004193 piperazinyl group Chemical group 0.000 claims 1
• 230000002265 prevention Effects 0.000 claims 1
• 230000000069 prophylactic effect Effects 0.000 claims 1
• 238000000034 method Methods 0.000 abstract description 75
• KQXRJVROLOXPNS-UHFFFAOYSA-N 2-[4-[(2-phenylindol-1-yl)methyl]phenoxy]ethanamine Chemical class C1=CC(OCCN)=CC=C1CN1C2=CC=CC=C2C=C1C1=CC=CC=C1 KQXRJVROLOXPNS-UHFFFAOYSA-N 0.000 abstract description 2
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 83
• 238000006243 chemical reaction Methods 0.000 description 53
• 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 44
• 239000000243 solution Substances 0.000 description 42
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• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 26
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