JP2005513027A5 - - Google Patents
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- Publication number
- JP2005513027A5 JP2005513027A5 JP2003545643A JP2003545643A JP2005513027A5 JP 2005513027 A5 JP2005513027 A5 JP 2005513027A5 JP 2003545643 A JP2003545643 A JP 2003545643A JP 2003545643 A JP2003545643 A JP 2003545643A JP 2005513027 A5 JP2005513027 A5 JP 2005513027A5
- Authority
- JP
- Japan
- Prior art keywords
- benzopyran
- dihydro
- cyclopentyl
- compound
- hydroxy
- Prior art date
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims description 33
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- -1 (+)-2- (4-hydroxyphenyl) -5-hydroxy-cyclopentyl Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 150000001408 amides Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 15
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims 1
- 102000000509 Estrogen Receptor beta Human genes 0.000 claims 1
- 108010041356 Estrogen Receptor beta Proteins 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- KSOVGRCOLZZTPF-QMKUDKLTSA-N (1s,2s,3r,4r)-3-[[5-fluoro-2-[3-methyl-4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)F)=NC=1NC(C=C1C)=CC=C1N1CCN(C)CC1 KSOVGRCOLZZTPF-QMKUDKLTSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- JKOHQRYDHCWBQW-SWKXRBFHSA-N NC(c1ccc(C([C@H]2C3CCC2)Oc(cc2)c3cc2O)cc1)=O Chemical compound NC(c1ccc(C([C@H]2C3CCC2)Oc(cc2)c3cc2O)cc1)=O JKOHQRYDHCWBQW-SWKXRBFHSA-N 0.000 description 1
- XIESSJVMWNJCGZ-SWKXRBFHSA-N Oc1ccc(C([C@H]2C3CCC2)Oc(cc2)c3cc2O)cc1 Chemical compound Oc1ccc(C([C@H]2C3CCC2)Oc(cc2)c3cc2O)cc1 XIESSJVMWNJCGZ-SWKXRBFHSA-N 0.000 description 1
- FSYFYSFYUHBIHE-TXKKKEFDSA-N Oc1ccc(C([C@H]2C3CCC2)Oc2c3c(O)ccc2)cc1 Chemical compound Oc1ccc(C([C@H]2C3CCC2)Oc2c3c(O)ccc2)cc1 FSYFYSFYUHBIHE-TXKKKEFDSA-N 0.000 description 1
- XCZLBAHLLDZLTP-QTLYGJNZSA-N Oc1ccc([C@H]([C@H]2C3CCC2)Oc(cc2)c3cc2F)cc1 Chemical compound Oc1ccc([C@H]([C@H]2C3CCC2)Oc(cc2)c3cc2F)cc1 XCZLBAHLLDZLTP-QTLYGJNZSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33276601P | 2001-11-19 | 2001-11-19 | |
| US36362202P | 2002-03-11 | 2002-03-11 | |
| PCT/US2002/033622 WO2003044006A1 (en) | 2001-11-19 | 2002-11-07 | Substituted benzopyrans as selective estrogen receptor-beta agonists |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005513027A JP2005513027A (ja) | 2005-05-12 |
| JP2005513027A5 true JP2005513027A5 (enExample) | 2006-01-05 |
| JP4381810B2 JP4381810B2 (ja) | 2009-12-09 |
Family
ID=26988373
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003545643A Expired - Fee Related JP4381810B2 (ja) | 2001-11-19 | 2002-11-07 | 選択的エストロゲン受容体βアゴニストとしての置換ベンゾピラン |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US7217734B2 (enExample) |
| EP (1) | EP1448544B1 (enExample) |
| JP (1) | JP4381810B2 (enExample) |
| KR (1) | KR100950616B1 (enExample) |
| CN (1) | CN1312147C (enExample) |
| AT (1) | ATE362471T1 (enExample) |
| AU (1) | AU2002359283B2 (enExample) |
| CA (1) | CA2467013C (enExample) |
| CY (1) | CY1106726T1 (enExample) |
| DE (1) | DE60220179T2 (enExample) |
| DK (1) | DK1448544T3 (enExample) |
| EA (1) | EA007382B1 (enExample) |
| EC (1) | ECSP045113A (enExample) |
| ES (1) | ES2286322T3 (enExample) |
| HR (1) | HRP20040439A2 (enExample) |
| HU (1) | HU229351B1 (enExample) |
| IL (3) | IL161325A0 (enExample) |
| MX (1) | MXPA04004703A (enExample) |
| NO (1) | NO328563B1 (enExample) |
| NZ (1) | NZ531850A (enExample) |
| PL (1) | PL205733B1 (enExample) |
| PT (1) | PT1448544E (enExample) |
| WO (1) | WO2003044006A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7279499B2 (en) | 2003-04-21 | 2007-10-09 | Eli Lilly And Company | Substituted benzopyrans as selective estrogen receptor-beta agonists |
| EP1626974B1 (en) * | 2003-04-21 | 2008-08-27 | Eli Lilly And Company | Substituted benzopyrans as selective estrogen receptor-beta agonists |
| JP2008512458A (ja) | 2004-09-07 | 2008-04-24 | ワイス | ６Ｈ−［１］ベンゾピラノ［４，３−ｂ］キノリン及びエストロゲン様物質としてのそれらの使用 |
| ATE504582T1 (de) * | 2004-10-18 | 2011-04-15 | Lilly Co Eli | Substituierte benzopyrane als selektive östrogenrezeptor-beta-agonisten |
| US20060166933A1 (en) * | 2004-11-18 | 2006-07-27 | Jain Nareshkumar F | Novel 2H-chromene derivatives as selective estrogen receptor modulators |
| US8093302B2 (en) | 2005-02-15 | 2012-01-10 | Eli Lilly And Company | Substituted tetralins as selective estrogen receptor-β agonists |
| US9604931B2 (en) | 2007-01-22 | 2017-03-28 | Gtx, Inc. | Nuclear receptor binding agents |
| US9623021B2 (en) | 2007-01-22 | 2017-04-18 | Gtx, Inc. | Nuclear receptor binding agents |
| US8063102B2 (en) | 2009-03-13 | 2011-11-22 | N.V. Organon | Tetrahydronaphthalen-2-ol derivatives |
| TW201043595A (en) | 2009-03-13 | 2010-12-16 | Organon Nv | Tetrahydronaphthalen-2-ol derivatives |
| CN105960236A (zh) | 2013-12-05 | 2016-09-21 | 卡罗医药股份公司 | 用于治疗间皮瘤的雌激素受体β激动剂 |
| JP6978420B2 (ja) | 2015-09-17 | 2021-12-08 | オハイオ・ステート・イノヴェーション・ファウンデーション | カルボラン化合物及びその使用方法 |
| WO2021183760A1 (en) * | 2020-03-11 | 2021-09-16 | Ohio State Innovation Foundation | Methods of modulating t-cell activation using estrogen receptor beta (erβ) agonists |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3901926A (en) * | 1973-04-02 | 1975-08-26 | Abbott Lab | Alkylphenyl benzopyrans |
| EP0935000A3 (en) | 1995-09-08 | 1999-09-08 | Karo Bio Ab | Orphan receptor |
| AU8102398A (en) * | 1997-07-09 | 1999-02-08 | Central Drug Research Institute | (dl)-2,3-diaryl-2h-1-benzopyrans |
| US6593322B1 (en) | 1999-03-17 | 2003-07-15 | Signal Pharmaceuticals, Inc. | Compounds and methods for modulation of estrogen receptors |
| JP2003521468A (ja) | 1999-03-17 | 2003-07-15 | シグナル ファーマシューティカルズ， インコーポレイテッド | エストロゲンレセプタを変調させるための化合物及び方法 |
| TR200102992T2 (tr) | 1999-04-16 | 2004-12-21 | Astrazeneca Ab | ß östrojen reseptörü ligandları. |
| CA2396059A1 (en) | 1999-12-30 | 2001-07-12 | Signal Pharmaceuticals, Inc. | Compounds and methods for modulation of estrogen receptors |
| US7214706B2 (en) * | 2000-03-01 | 2007-05-08 | Akzo Nobel N.V. | Chroman derivatives as estrogenic compounds |
| ES2293986T3 (es) | 2000-03-27 | 2008-04-01 | N.V. Organon | Compuestos no esteroides tetraciclicos para tratamientos relacionados con el estrogeno. |
| GB2361642A (en) | 2000-10-24 | 2001-10-31 | Karobio Ab | Estrogen receptor beta (ERbeta) agonists for use in cancer treatment |
| UA83620C2 (ru) | 2001-12-05 | 2008-08-11 | Уайт | Замещенные бензоксазолы и их аналоги как эстрогенные агенты |
| TWI306450B (en) | 2001-12-13 | 2009-02-21 | Wyeth Corp | Substituted phenyl naphthalenes as estrogenic agents |
| US6630508B1 (en) * | 2002-02-11 | 2003-10-07 | Eli Lilly And Company | Substituted benzopyrans as selective estrogen receptor β agonists |
-
2002
- 2002-11-07 DE DE60220179T patent/DE60220179T2/de not_active Expired - Lifetime
- 2002-11-07 IL IL16132502A patent/IL161325A0/xx unknown
- 2002-11-07 PT PT02793806T patent/PT1448544E/pt unknown
- 2002-11-07 US US10/493,092 patent/US7217734B2/en not_active Expired - Fee Related
- 2002-11-07 EP EP02793806A patent/EP1448544B1/en not_active Expired - Lifetime
- 2002-11-07 CN CNB028229916A patent/CN1312147C/zh not_active Expired - Fee Related
- 2002-11-07 JP JP2003545643A patent/JP4381810B2/ja not_active Expired - Fee Related
- 2002-11-07 HU HU0402628A patent/HU229351B1/hu not_active IP Right Cessation
- 2002-11-07 DK DK02793806T patent/DK1448544T3/da active
- 2002-11-07 AT AT02793806T patent/ATE362471T1/de active
- 2002-11-07 PL PL374510A patent/PL205733B1/pl unknown
- 2002-11-07 WO PCT/US2002/033622 patent/WO2003044006A1/en not_active Ceased
- 2002-11-07 MX MXPA04004703A patent/MXPA04004703A/es active IP Right Grant
- 2002-11-07 CA CA2467013A patent/CA2467013C/en not_active Expired - Fee Related
- 2002-11-07 HR HR20040439A patent/HRP20040439A2/hr not_active Application Discontinuation
- 2002-11-07 NZ NZ531850A patent/NZ531850A/en not_active IP Right Cessation
- 2002-11-07 EA EA200400695A patent/EA007382B1/ru not_active IP Right Cessation
- 2002-11-07 KR KR1020047007563A patent/KR100950616B1/ko not_active Expired - Fee Related
- 2002-11-07 AU AU2002359283A patent/AU2002359283B2/en not_active Ceased
- 2002-11-07 ES ES02793806T patent/ES2286322T3/es not_active Expired - Lifetime
-
2004
- 2004-04-08 IL IL161325A patent/IL161325A/en not_active IP Right Cessation
- 2004-05-19 EC EC2004005113A patent/ECSP045113A/es unknown
- 2004-06-18 NO NO20042583A patent/NO328563B1/no not_active IP Right Cessation
-
2007
- 2007-07-13 CY CY20071100932T patent/CY1106726T1/el unknown
- 2007-09-10 IL IL185867A patent/IL185867A/en not_active IP Right Cessation
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