ES2259376T3

ES2259376T3 - 1,2,3,4-tetrahidroquinolinas 2-sustituidas y sus derivados, composiciones y procedimientos.

1,2,3,4-tetrahidroquinolinas 2-sustituidas y sus derivados, composiciones y procedimientos.

Info

Publication number: ES2259376T3
Authority: ES; Spain
Prior art keywords: ethoxy; piperidin; phenyl; estrogen; compound
Prior art date: 2001-05-22
Legal status : Expired - Lifetime

Application number

ES02746308T

Other languages

English (en)

Spanish (es)

Inventor

Owen Brendan Wallace

Current Assignee

Eli Lilly and Co

Original Assignee

Eli Lilly and Co

Priority date

2001-05-22

Filing date

2002-05-09

Publication date

2006-10-01

2002-05-09 Application filed by Eli Lilly and Co filed Critical Eli Lilly and Co

2006-10-01 Application granted granted Critical

2006-10-01 Publication of ES2259376T3 publication Critical patent/ES2259376T3/es

2022-05-09 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000000034 method Methods 0.000 title abstract description 48
239000000203 mixture Substances 0.000 title description 31
239000000262 estrogen Substances 0.000 claims abstract description 70
229940011871 estrogen Drugs 0.000 claims abstract description 68
-1 2-substituted 1,2,3,4-tetrahydroquinolin-6-ols Chemical class 0.000 claims abstract description 32
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 26
201000010099 disease Diseases 0.000 claims abstract description 23
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 claims abstract description 18
239000000583 progesterone congener Substances 0.000 claims abstract description 18
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
230000006461 physiological response Effects 0.000 claims abstract description 5
150000001875 compounds Chemical class 0.000 claims description 115
150000003839 salts Chemical class 0.000 claims description 38
238000002360 preparation method Methods 0.000 claims description 21
125000000217 alkyl group Chemical group 0.000 claims description 19
206010006187 Breast cancer Diseases 0.000 claims description 13
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206010028980 Neoplasm Diseases 0.000 claims description 11
208000001132 Osteoporosis Diseases 0.000 claims description 9
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IQBSKHUUKFFBOG-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]-3,4-dihydro-2h-quinolin-6-ol Chemical compound C1=CC(O)=CC=C1C1N(CC=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2CC1 IQBSKHUUKFFBOG-UHFFFAOYSA-N 0.000 claims description 7
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125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 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
VPHDBSKPCLXHJV-UHFFFAOYSA-N 2-(3-hydroxyphenyl)-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]-3,4-dihydro-2h-quinolin-6-ol Chemical compound OC1=CC=CC(C2N(C3=CC=C(O)C=C3CC2)CC=2C=CC(OCCN3CCCCC3)=CC=2)=C1 VPHDBSKPCLXHJV-UHFFFAOYSA-N 0.000 claims description 5
QVZRHXCUIQTJGV-UHFFFAOYSA-N 6-methoxy-2-(3-methoxyphenyl)-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]-3,4-dihydro-2h-quinoline Chemical compound COC1=CC=CC(C2N(C3=CC=C(OC)C=C3CC2)CC=2C=CC(OCCN3CCCCC3)=CC=2)=C1 QVZRHXCUIQTJGV-UHFFFAOYSA-N 0.000 claims description 5
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OQJYJENHHOZHPV-UHFFFAOYSA-N 2-phenyl-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]-3,4-dihydro-2h-quinolin-6-ol Chemical compound C=1C=CC=CC=1C1CCC2=CC(O)=CC=C2N1CC(C=C1)=CC=C1OCCN1CCCCC1 OQJYJENHHOZHPV-UHFFFAOYSA-N 0.000 claims description 4
SBYKRIWWAKRTSL-UHFFFAOYSA-N 6-methoxy-2-phenyl-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]-3,4-dihydro-2h-quinoline Chemical compound C=1C=CC=CC=1C1CCC2=CC(OC)=CC=C2N1CC(C=C1)=CC=C1OCCN1CCCCC1 SBYKRIWWAKRTSL-UHFFFAOYSA-N 0.000 claims description 4
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DMRMYRIKDDOVCY-UHFFFAOYSA-N (6-hydroxy-2-phenyl-3,4-dihydro-2h-quinolin-1-yl)-[4-(2-piperidin-1-ylethoxy)phenyl]methanone Chemical compound C1CC2=CC(O)=CC=C2N(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C1C1=CC=CC=C1 DMRMYRIKDDOVCY-UHFFFAOYSA-N 0.000 claims description 3
ZGLRJOMWQPLWAB-UHFFFAOYSA-N (6-methoxy-2-phenyl-3,4-dihydro-2h-quinolin-1-yl)-[4-(2-piperidin-1-ylethoxy)phenyl]methanone Chemical compound C1CC2=CC(OC)=CC=C2N(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C1C1=CC=CC=C1 ZGLRJOMWQPLWAB-UHFFFAOYSA-N 0.000 claims description 3
YXEHOUBMVAITRA-UHFFFAOYSA-N 6-methoxy-2-(4-methoxyphenyl)-1-[[4-(2-pyrrolidin-1-ylethoxy)phenyl]methyl]-3,4-dihydro-2h-quinoline Chemical compound C1=CC(OC)=CC=C1C1N(CC=2C=CC(OCCN3CCCC3)=CC=2)C2=CC=C(OC)C=C2CC1 YXEHOUBMVAITRA-UHFFFAOYSA-N 0.000 claims description 3
KUBYSGIGKNDGJE-UHFFFAOYSA-N [6-hydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-quinolin-1-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone Chemical compound C1=CC(O)=CC=C1C1N(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2CC1 KUBYSGIGKNDGJE-UHFFFAOYSA-N 0.000 claims description 3
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239000002585 base Substances 0.000 description 11
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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 11
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