SK281737B6 - 2-fenylindolové zlúčeniny, farmaceutický prostriedok s ich obsahom a ich použitie - Google Patents

2-fenylindolové zlúčeniny, farmaceutický prostriedok s ich obsahom a ich použitie Download PDF

Info

Publication number: SK281737B6
Authority: SK; Slovakia
Prior art keywords: benzyl; methyl; ethoxy; compound; pharmaceutically acceptable
Prior art date: 1996-04-19

Application number

SK472-97A

Other languages

English (en)

Slovak (sk)

Other versions

SK47297A3 (en

Inventor

Chris Paul Miller

Michael David Collini

Bach Dinh Tran

Arthur Attilio Santilli

Original Assignee

American Home Products Corporation

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.)

1996-04-19

Filing date

1997-04-15

Publication date

2001-07-10

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=27092026&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=SK281737(B6) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1997-04-04 Priority claimed from US08/833,271 external-priority patent/US5998402A/en

1997-04-15 Application filed by American Home Products Corporation filed Critical American Home Products Corporation

1997-11-05 Publication of SK47297A3 publication Critical patent/SK47297A3/sk

2001-07-10 Publication of SK281737B6 publication Critical patent/SK281737B6/sk

Links

239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 5
KLLLJCACIRKBDT-UHFFFAOYSA-N 2-phenyl-1H-indole Chemical class N1C2=CC=CC=C2C=C1C1=CC=CC=C1 KLLLJCACIRKBDT-UHFFFAOYSA-N 0.000 title claims description 4
150000001875 compounds Chemical class 0.000 claims abstract description 180
238000011282 treatment Methods 0.000 claims abstract description 25
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 13
210000001519 tissue Anatomy 0.000 claims abstract description 11
201000010099 disease Diseases 0.000 claims abstract description 10
239000003814 drug Substances 0.000 claims abstract description 7
206010030247 Oestrogen deficiency Diseases 0.000 claims abstract description 5
230000035755 proliferation Effects 0.000 claims abstract description 4
230000004044 response Effects 0.000 claims abstract description 4
208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 3
230000002159 abnormal effect Effects 0.000 claims abstract description 3
238000011161 development Methods 0.000 claims abstract description 3
230000002357 endometrial effect Effects 0.000 claims abstract description 3
230000002265 prevention Effects 0.000 claims abstract description 3
-1 2-phenylindole compound Chemical class 0.000 claims description 195
150000003839 salts Chemical class 0.000 claims description 95
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 89
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 76
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 54
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 54
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 42
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 38
125000004093 cyano group Chemical group *C#N 0.000 claims description 26
229910052736 halogen Inorganic materials 0.000 claims description 23
150000002367 halogens Chemical class 0.000 claims description 23
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
125000000217 alkyl group Chemical group 0.000 claims description 22
229910052739 hydrogen Inorganic materials 0.000 claims description 22
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
125000003282 alkyl amino group Chemical group 0.000 claims description 19
125000001424 substituent group Chemical group 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
125000004953 trihalomethyl group Chemical group 0.000 claims description 14
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 13
229910052799 carbon Inorganic materials 0.000 claims description 12
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
125000004951 trihalomethoxy group Chemical group 0.000 claims description 11
150000005215 alkyl ethers Chemical class 0.000 claims description 9
150000002148 esters Chemical class 0.000 claims description 9
125000005842 heteroatom Chemical group 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 7
229920006395 saturated elastomer Polymers 0.000 claims description 7
MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical class C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 claims description 6
125000000623 heterocyclic group Chemical group 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
LMIQERWZRIFWNZ-UHFFFAOYSA-N 5-hydroxyindole Chemical compound OC1=CC=C2NC=CC2=C1 LMIQERWZRIFWNZ-UHFFFAOYSA-N 0.000 claims description 5
125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 4
206010065687 Bone loss Diseases 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
125000004122 cyclic group Chemical group 0.000 claims description 4
150000002170 ethers Chemical class 0.000 claims description 4
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 4
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 description 3
FBCLHHRZKNDZAZ-UHFFFAOYSA-N 3-methyl-5-phenylmethoxy-2-(4-phenylmethoxyphenyl)-1-[[4-(3-piperidin-1-ylpropoxy)phenyl]methyl]indole Chemical compound 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 3
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
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 description 2
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 description 2
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 description 2
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 description 2
ZAHXUDHYBXTZAN-UHFFFAOYSA-N 1-[[4-[2-(azepan-1-yl)ethoxy]phenyl]methyl]-5-phenylmethoxy-2-(4-phenylmethoxyphenyl)indole-3-carbonitrile Chemical compound C=1C=C(OCCN2CCCCCC2)C=CC=1CN1C2=CC=C(OCC=3C=CC=CC=3)C=C2C(C#N)=C1C(C=C1)=CC=C1OCC1=CC=CC=C1 ZAHXUDHYBXTZAN-UHFFFAOYSA-N 0.000 claims description 2
UDYXSEQZOCRRKY-UHFFFAOYSA-N 1-[[4-[2-[butyl(methyl)amino]ethoxy]phenyl]methyl]-2-(4-hydroxyphenyl)-3-methylindol-5-ol Chemical compound C1=CC(OCCN(C)CCCC)=CC=C1CN1C2=CC=C(O)C=C2C(C)=C1C1=CC=C(O)C=C1 UDYXSEQZOCRRKY-UHFFFAOYSA-N 0.000 claims description 2
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 description 2
QFOMEAKDJGTPOK-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-3-methyl-1-[[4-[2-(2-methylpiperidin-1-yl)ethoxy]phenyl]methyl]indol-5-ol Chemical compound CC1CCCCN1CCOC(C=C1)=CC=C1CN1C2=CC=C(O)C=C2C(C)=C1C1=CC=C(O)C=C1 QFOMEAKDJGTPOK-UHFFFAOYSA-N 0.000 claims description 2
BJPSMLQKBYXZHY-UHFFFAOYSA-N 3-chloro-2-(4-hydroxyphenyl)-1-[[4-(2-pyrrolidin-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=C1OCCN1CCCC1 BJPSMLQKBYXZHY-UHFFFAOYSA-N 0.000 claims description 2
HTOSZBPMJWNECY-UHFFFAOYSA-N 3-methyl-1-[[4-[2-(2-methylpiperidin-1-yl)ethoxy]phenyl]methyl]-5-phenylmethoxy-2-(4-phenylmethoxyphenyl)indole Chemical compound CC1CCCCN1CCOC(C=C1)=CC=C1CN1C2=CC=C(OCC=3C=CC=CC=3)C=C2C(C)=C1C(C=C1)=CC=C1OCC1=CC=CC=C1 HTOSZBPMJWNECY-UHFFFAOYSA-N 0.000 claims description 2
HRWLZMUMZNLJIV-UHFFFAOYSA-N 3-methyl-1-[[4-[2-(3-methylpiperidin-1-yl)ethoxy]phenyl]methyl]-5-phenylmethoxy-2-(4-phenylmethoxyphenyl)indole Chemical compound C1C(C)CCCN1CCOC(C=C1)=CC=C1CN1C2=CC=C(OCC=3C=CC=CC=3)C=C2C(C)=C1C(C=C1)=CC=C1OCC1=CC=CC=C1 HRWLZMUMZNLJIV-UHFFFAOYSA-N 0.000 claims description 2
JCMIMFGRGKKZBR-UHFFFAOYSA-N 4-[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=CC=C2C(C)=C1C1=CC=C(O)C=C1 JCMIMFGRGKKZBR-UHFFFAOYSA-N 0.000 claims description 2
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
125000004423 acyloxy group Chemical group 0.000 claims description 2
125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
AEYIMAVEKNBQRO-UHFFFAOYSA-N n-[2-[4-[[3-methyl-5-phenylmethoxy-2-(4-phenylmethoxyphenyl)indol-1-yl]methyl]phenoxy]ethyl]cyclohexanamine Chemical compound C=1C=C(OCCNC2CCCCC2)C=CC=1CN1C2=CC=C(OCC=3C=CC=CC=3)C=C2C(C)=C1C(C=C1)=CC=C1OCC1=CC=CC=C1 AEYIMAVEKNBQRO-UHFFFAOYSA-N 0.000 claims description 2
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
208000011580 syndromic disease Diseases 0.000 claims description 2
SMYMDRJWEFCCCI-UHFFFAOYSA-N trichloro(trichloromethoxy)methane Chemical compound ClC(Cl)(Cl)OC(Cl)(Cl)Cl SMYMDRJWEFCCCI-UHFFFAOYSA-N 0.000 claims description 2
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
241000124008 Mammalia Species 0.000 claims 4
125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 2
125000003545 alkoxy group Chemical group 0.000 claims 2
MZTIQFQXCDTRSS-UHFFFAOYSA-N 1-[[3-methoxy-4-(2-piperidin-1-ylethoxy)phenyl]methyl]-3-methyl-5-phenylmethoxy-2-(4-phenylmethoxyphenyl)indole Chemical compound C=1C=C(OCCN2CCCCC2)C(OC)=CC=1CN(C1=CC=2)C(C=3C=CC(OCC=4C=CC=CC=4)=CC=3)=C(C)C1=CC=2OCC1=CC=CC=C1 MZTIQFQXCDTRSS-UHFFFAOYSA-N 0.000 claims 1
WINHDAHOVHUMMK-UHFFFAOYSA-N 1-[[4-[2-(azepan-1-yl)ethoxy]phenyl]methyl]-2-(4-ethoxyphenyl)-3-methylindol-5-ol Chemical compound C1=CC(OCC)=CC=C1C1=C(C)C2=CC(O)=CC=C2N1CC(C=C1)=CC=C1OCCN1CCCCCC1 WINHDAHOVHUMMK-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
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 1
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 1
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 1
FNNWTXMUBMHNOD-UHFFFAOYSA-N 1-methylindol-5-ol Chemical compound OC1=CC=C2N(C)C=CC2=C1 FNNWTXMUBMHNOD-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
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 1
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 1
LYDTYRQEQHFCTJ-UHFFFAOYSA-N 3-chloro-2-(4-hydroxyphenyl)-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]indol-5-ol Chemical compound C1=CC(O)=CC=C1C1=C(Cl)C2=CC(O)=CC=C2N1CC(C=C1)=CC=C1OCCN1CCCCC1 LYDTYRQEQHFCTJ-UHFFFAOYSA-N 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
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
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
MIQSJGVXNZHDRU-UHFFFAOYSA-N 5-phenylmethoxy-2-(4-phenylmethoxyphenyl)-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]indole Chemical compound C=1C=C(CN2C3=CC=C(OCC=4C=CC=CC=4)C=C3C=C2C=2C=CC(OCC=3C=CC=CC=3)=CC=2)C=CC=1OCCN1CCCCC1 MIQSJGVXNZHDRU-UHFFFAOYSA-N 0.000 claims 1
BRPCDENFWNNQQK-UHFFFAOYSA-N CC1=C(N(C2=CC=CC=C12)CC3=CC(=C(C=C3)OCCN4CCCCCC4)OC)C5=CC=C(C=C5)O Chemical compound CC1=C(N(C2=CC=CC=C12)CC3=CC(=C(C=C3)OCCN4CCCCCC4)OC)C5=CC=C(C=C5)O BRPCDENFWNNQQK-UHFFFAOYSA-N 0.000 claims 1
FCISIDUVLHBQOY-UHFFFAOYSA-N CC1=C(N(C2=CC=CC=C12)CC3=CC=C(C=C3)OCCN4CCC(CC4)O)C5=CC=C(C=C5)O Chemical compound CC1=C(N(C2=CC=CC=C12)CC3=CC=C(C=C3)OCCN4CCC(CC4)O)C5=CC=C(C=C5)O FCISIDUVLHBQOY-UHFFFAOYSA-N 0.000 claims 1
VOEBBZZZNRIFGA-UHFFFAOYSA-N CC1=CN(C2=C1C=C(C=C2)O)C3=CC=CC=C3O Chemical compound CC1=CN(C2=C1C=C(C=C2)O)C3=CC=CC=C3O VOEBBZZZNRIFGA-UHFFFAOYSA-N 0.000 claims 1
HNVSAZWKVSYDOE-UHFFFAOYSA-N CC1CCCN(C1)CCOC2=CC=C(C=C2)CN3C4=CC=CC=C4C(=C3C5=CC=C(C=C5)O)C Chemical compound CC1CCCN(C1)CCOC2=CC=C(C=C2)CN3C4=CC=CC=C4C(=C3C5=CC=C(C=C5)O)C HNVSAZWKVSYDOE-UHFFFAOYSA-N 0.000 claims 1
LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-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
238000000034 method Methods 0.000 abstract description 74
239000000262 estrogen Substances 0.000 abstract description 18
210000000988 bone and bone Anatomy 0.000 abstract description 14
238000002360 preparation method Methods 0.000 abstract description 7
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
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 489
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 87
239000000243 solution Substances 0.000 description 40
230000015572 biosynthetic process Effects 0.000 description 39
239000011541 reaction mixture Substances 0.000 description 39
238000003786 synthesis reaction Methods 0.000 description 34
235000019439 ethyl acetate Nutrition 0.000 description 33
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 31
239000007787 solid Substances 0.000 description 30
238000006243 chemical reaction Methods 0.000 description 29
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 28
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 27
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
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XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
229940054269 sodium pyruvate Drugs 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000003270 steroid hormone Substances 0.000 description 1
230000003637 steroidlike Effects 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000010414 supernatant solution Substances 0.000 description 1
230000000153 supplemental effect Effects 0.000 description 1
230000009469 supplementation Effects 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000007916 tablet composition Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
FQZYTYWMLGAPFJ-OQKDUQJOSA-N tamoxifen citrate Chemical compound [H+].[H+].[H+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 FQZYTYWMLGAPFJ-OQKDUQJOSA-N 0.000 description 1
229960003454 tamoxifen citrate Drugs 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000004001 thioalkyl group Chemical group 0.000 description 1
210000002303 tibia Anatomy 0.000 description 1
238000012546 transfer Methods 0.000 description 1
238000009901 transfer hydrogenation reaction Methods 0.000 description 1
230000001228 trophic effect Effects 0.000 description 1
239000012588 trypsin Substances 0.000 description 1
206010046811 uterine polyp Diseases 0.000 description 1
MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
235000012141 vanillin Nutrition 0.000 description 1
FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000001993 wax Substances 0.000 description 1
230000004584 weight gain Effects 0.000 description 1
235000019786 weight gain Nutrition 0.000 description 1
238000005550 wet granulation Methods 0.000 description 1
239000000230 xanthan gum Substances 0.000 description 1
235000010493 xanthan gum Nutrition 0.000 description 1
229920001285 xanthan gum Polymers 0.000 description 1
229940082509 xanthan gum Drugs 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- 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
- 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
- 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
- A61P5/30—Oestrogens
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Endocrinology (AREA)
Physical Education & Sports Medicine (AREA)
Diabetes (AREA)
Reproductive Health (AREA)
Orthopedic Medicine & Surgery (AREA)
Heart & Thoracic Surgery (AREA)
Rheumatology (AREA)
Urology & Nephrology (AREA)
Cardiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Indole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

SK472-97A 1996-04-19 1997-04-15 2-fenylindolové zlúčeniny, farmaceutický prostriedok s ich obsahom a ich použitie SK281737B6 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US63397496A	1996-04-19	1996-04-19
US08/833,271 US5998402A (en)	1996-04-19	1997-04-04	2-phenyl-1-[4-(2-aminoethoxy)-benzyl]-indoles as estrogenic agents

Publications (2)

Publication Number	Publication Date
SK47297A3 SK47297A3 (en)	1997-11-05
SK281737B6 true SK281737B6 (sk)	2001-07-10

Family

ID=27092026

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK472-97A SK281737B6 (sk)	1996-04-19	1997-04-15	2-fenylindolové zlúčeniny, farmaceutický prostriedok s ich obsahom a ich použitie

Country Status (26)

Country	Link
EP (1)	EP0802183B1 (fr)
JP (1)	JP4093611B2 (fr)
KR (1)	KR100480193B1 (fr)
CN (1)	CN1106383C (fr)
AR (1)	AR011503A1 (fr)
AT (1)	ATE206701T1 (fr)
AU (1)	AU710149B2 (fr)
BR (1)	BRPI9715334B8 (fr)
CO (1)	CO4900051A1 (fr)
CY (2)	CY2325B1 (fr)
CZ (1)	CZ291701B6 (fr)
DE (2)	DE122009000061I1 (fr)
DK (1)	DK0802183T3 (fr)
EA (1)	EA001448B1 (fr)
ES (1)	ES2162198T3 (fr)
FR (1)	FR09C0048I2 (fr)
HU (1)	HU227077B1 (fr)
IL (1)	IL120701A (fr)
LU (1)	LU91608I2 (fr)
MX (1)	MX9702865A (fr)
NL (1)	NL300416I2 (fr)
NO (2)	NO309564B1 (fr)
NZ (1)	NZ314601A (fr)
PT (1)	PT802183E (fr)
SK (1)	SK281737B6 (fr)
UA (1)	UA48148C2 (fr)

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1997
- 1997-04-15 NZ NZ314601A patent/NZ314601A/en not_active IP Right Cessation
- 1997-04-15 AT AT97302576T patent/ATE206701T1/de active
- 1997-04-15 PT PT97302576T patent/PT802183E/pt unknown
- 1997-04-15 ES ES97302576T patent/ES2162198T3/es not_active Expired - Lifetime
- 1997-04-15 DK DK97302576T patent/DK0802183T3/da active
- 1997-04-15 EP EP97302576A patent/EP0802183B1/fr not_active Expired - Lifetime
- 1997-04-15 DE DE122009000061C patent/DE122009000061I1/de active Pending
- 1997-04-15 SK SK472-97A patent/SK281737B6/sk not_active IP Right Cessation
- 1997-04-15 DE DE69707189T patent/DE69707189T2/de not_active Expired - Lifetime
- 1997-04-17 CZ CZ19971175A patent/CZ291701B6/cs not_active IP Right Cessation
- 1997-04-17 UA UA97041833A patent/UA48148C2/uk unknown
- 1997-04-17 AU AU18920/97A patent/AU710149B2/en not_active Expired
- 1997-04-18 IL IL12070197A patent/IL120701A/xx active Protection Beyond IP Right Term
- 1997-04-18 CO CO97020584A patent/CO4900051A1/es unknown
- 1997-04-18 NO NO971815A patent/NO309564B1/no not_active IP Right Cessation
- 1997-04-18 EA EA199700044A patent/EA001448B1/ru not_active IP Right Cessation
- 1997-04-18 AR ARP970101580A patent/AR011503A1/es active IP Right Grant
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- 1997-04-18 JP JP10156397A patent/JP4093611B2/ja not_active Expired - Lifetime
- 1997-04-18 KR KR1019970014894A patent/KR100480193B1/ko not_active Expired - Lifetime
- 1997-04-18 CN CN97113496A patent/CN1106383C/zh not_active Expired - Lifetime
- 1997-04-18 HU HU9700777A patent/HU227077B1/hu active Protection Beyond IP Right Term
- 1997-04-22 BR BRPI9715334A patent/BRPI9715334B8/pt not_active IP Right Cessation
2003
- 2003-04-08 CY CY0300038A patent/CY2325B1/xx unknown
2009
- 2009-09-23 LU LU91608C patent/LU91608I2/fr unknown
- 2009-09-28 NL NL300416C patent/NL300416I2/nl unknown
- 2009-09-30 FR FR09C0048C patent/FR09C0048I2/fr active Active
- 2009-09-30 CY CY2009016C patent/CY2009016I2/el unknown
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Also Published As

Publication number	Publication date
SK47297A3 (en)	1997-11-05
FR09C0048I1 (fr)	2009-06-11
CY2009016I1 (el)	2010-07-28
FR09C0048I2 (fr)	2010-06-11
HK1002863A1 (en)	1998-09-25
UA48148C2 (uk)	2002-08-15
MX9702865A (es)	1998-05-31
AR011503A1 (es)	2000-08-30
CY2325B1 (en)	2003-11-14
HU9700777D0 (en)	1997-06-30
CN1106383C (zh)	2003-04-23
HU227077B1 (en)	2010-06-28
CO4900051A1 (es)	2000-03-27
JPH1036346A (ja)	1998-02-10
EA001448B1 (ru)	2001-04-23
PT802183E (pt)	2002-03-28
CN1170719A (zh)	1998-01-21
EP0802183A1 (fr)	1997-10-22
DK0802183T3 (da)	2002-02-04
NL300416I1 (nl)	2009-12-01
HUP9700777A3 (en)	2000-04-28
CZ291701B6 (cs)	2003-05-14
NL300416I2 (nl)	2010-02-01
IL120701A (en)	2005-09-25
LU91608I2 (fr)	2009-11-23
ATE206701T1 (de)	2001-10-15
EA199700044A1 (ru)	1997-12-30
KR100480193B1 (ko)	2005-08-30
KR970069037A (ko)	1997-11-07
CZ117597A3 (en)	1997-11-12
NZ314601A (en)	1999-09-29
EP0802183B1 (fr)	2001-10-10
DE69707189D1 (de)	2001-11-15
CY2009016I2 (el)	2010-07-28
AU1892097A (en)	1997-10-23
NO971815L (no)	1997-10-20
DE69707189T2 (de)	2002-06-20
NO309564B1 (no)	2001-02-19
NO971815D0 (no)	1997-04-18
ES2162198T3 (es)	2001-12-16
NO2009025I1 (no)	2009-11-30
BRPI9715334B8 (pt)	2021-05-25
IL120701A0 (en)	1997-09-30
NO2009025I2 (no)	2010-11-22
JP4093611B2 (ja)	2008-06-04
AU710149B2 (en)	1999-09-16
BR9715334B1 (pt)	2012-09-04
DE122009000061I1 (de)	2009-12-31
HUP9700777A2 (hu)	1999-06-28

Publication	Publication Date	Title
SK281737B6 (sk)	2001-07-10	2-fenylindolové zlúčeniny, farmaceutický prostriedok s ich obsahom a ich použitie
US6225308B1 (en)	2001-05-01	Tissue selective compounds in the treatment of prostate cancer or benign prostate hypertrophy
US20030203883A1 (en)	2003-10-30	2-phenyl-1-[4-(2-aminoethoxy)-benzyl]-indole and estrogen formulations
SK284666B6 (sk)	2005-08-04	Farmaceutický prostriedok obsahujúci indolové zlúčeniny a estrogény a jeho použitie
CA2203078C (fr)	2006-12-05	2-phenyl-1-[4-(2-aminoethoxy)-benzyl]indoles en tant qu'agents oestrogeniques
HK1002863B (en)	2002-02-15	Estrogenic agents
CA2558821A1 (fr)	1998-10-04	2-phenyl-1-[4-(2-aminoethoxy)-benzyl]indoles en tant qu'agents oestrogeniques
MXPA00011178A (en)	2001-07-31	2-phenyl-1-[4-(2-aminoethoxy)-benzyl]-indole in combination with estrogens

Legal Events

Date	Code	Title	Description
2017-06-02	MK4A	Patent expired	Expiry date: 20170415