NO317055B1 - Benzopyran-inneholdende forbindelser, anvendelse av samme for fremstilling av medikament og farmasoytisk sammensetning innbefattende samme - Google Patents
Benzopyran-inneholdende forbindelser, anvendelse av samme for fremstilling av medikament og farmasoytisk sammensetning innbefattende samme Download PDFInfo
- Publication number
- NO317055B1 NO317055B1 NO19973836A NO973836A NO317055B1 NO 317055 B1 NO317055 B1 NO 317055B1 NO 19973836 A NO19973836 A NO 19973836A NO 973836 A NO973836 A NO 973836A NO 317055 B1 NO317055 B1 NO 317055B1
- Authority
- NO
- Norway
- Prior art keywords
- compound
- phenyl
- pharmaceutically acceptable
- estrogen
- hydroxyl
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 11
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US08/388,207 US6060503A (en) | 1991-12-02 | 1995-02-21 | Benzopyran-containing compounds and method for their use |
PCT/CA1996/000097 WO1996026201A1 (en) | 1995-02-21 | 1996-02-20 | Benzopyran-containing compounds and method for their use |
Publications (3)
Publication Number | Publication Date |
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NO973836D0 NO973836D0 (no) | 1997-08-20 |
NO973836L NO973836L (no) | 1997-08-20 |
NO317055B1 true NO317055B1 (no) | 2004-08-02 |
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Application Number | Title | Priority Date | Filing Date |
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NO19973836A NO317055B1 (no) | 1995-02-21 | 1997-08-20 | Benzopyran-inneholdende forbindelser, anvendelse av samme for fremstilling av medikament og farmasoytisk sammensetning innbefattende samme |
NO20035726A NO328598B1 (no) | 1995-02-21 | 2003-12-19 | Benzopyran-inneholdende forbindelser, anvendelse av samme for fremstilling av medikament samt farmasoytisk sammensetning innbefattende det samme |
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NO20035726A NO328598B1 (no) | 1995-02-21 | 2003-12-19 | Benzopyran-inneholdende forbindelser, anvendelse av samme for fremstilling av medikament samt farmasoytisk sammensetning innbefattende det samme |
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US (1) | US6060503A (tr) |
EP (2) | EP1167364B1 (tr) |
JP (1) | JPH11500133A (tr) |
KR (1) | KR100487647B1 (tr) |
CN (1) | CN1158274C (tr) |
AR (1) | AR004167A1 (tr) |
AT (2) | ATE239007T1 (tr) |
AU (1) | AU4660696A (tr) |
BR (1) | BR9607259A (tr) |
CA (1) | CA2212856C (tr) |
DE (2) | DE69627831T2 (tr) |
DK (2) | DK0811006T3 (tr) |
ES (2) | ES2199912T3 (tr) |
FI (1) | FI120940B (tr) |
HK (1) | HK1009440A1 (tr) |
HU (1) | HU227762B1 (tr) |
IL (2) | IL150767A (tr) |
MX (1) | MX9706345A (tr) |
MY (1) | MY117248A (tr) |
NO (2) | NO317055B1 (tr) |
NZ (1) | NZ301231A (tr) |
PL (1) | PL188076B1 (tr) |
PT (2) | PT1167364E (tr) |
RU (1) | RU2220143C2 (tr) |
TR (1) | TR199600144A2 (tr) |
TW (1) | TW434238B (tr) |
WO (1) | WO1996026201A1 (tr) |
ZA (1) | ZA961316B (tr) |
Families Citing this family (52)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU8102398A (en) * | 1997-07-09 | 1999-02-08 | Central Drug Research Institute | (dl)-2,3-diaryl-2h-1-benzopyrans |
AU8102498A (en) * | 1997-07-09 | 1999-02-08 | Central Drug Research Institute | Preparation of diaryl-benzopyrans |
TR200002784T2 (tr) | 1998-03-11 | 2000-12-21 | Endorecherche, Inc | Tip 5 ve tip 3 17beta-Hidroksisteroid dehidrojenaz inhibitörleri ve bunların kullanımı için metodlar |
US7005428B1 (en) | 1998-06-11 | 2006-02-28 | Endorecherche, Inc. | Medical uses of a selective estrogen receptor modulator in combination with sex steroid precursors |
US6465445B1 (en) | 1998-06-11 | 2002-10-15 | Endorecherche, Inc. | Medical uses of a selective estrogen receptor modulator in combination with sex steroid precursors |
KR20000001793A (ko) * | 1998-06-13 | 2000-01-15 | 이경하 | 신규한 벤조피란 또는 티오벤조피란 유도체 |
US6262270B1 (en) | 1998-08-14 | 2001-07-17 | Schering Corporation | Enantioselective synthesis |
ATE232525T1 (de) * | 1998-08-14 | 2003-02-15 | Schering Corp | Enanthioauswählende synthese |
AU2156800A (en) * | 1998-12-18 | 2000-07-12 | Schering Corporation | Oral antiestrogen pharmaceutical composition |
HU230543B1 (hu) * | 1999-07-06 | 2016-11-28 | Endorecherche, Inc. | Inzulinrezisztencia kezelésére és/vagy megakadályozására szolgáló gyógyszerkészítmények |
WO2001026651A2 (en) * | 1999-10-14 | 2001-04-19 | Endorecherche, Inc. | Selective estrogen receptor modulators in the treatment or reduction of the risk of acquiring hypertension, cardiovascular diseases, and insulin resistance |
CO5271709A1 (es) * | 2000-01-12 | 2003-04-30 | Pfizer Prod Inc | Composiciones y procedimientos para el y tratamiento de afecciones que responden a estrogenos |
DE10013782A1 (de) | 2000-03-15 | 2001-10-18 | Schering Ag | 4-Fluoralkyl-2H-benzopyrane mit antiestrogener Wirksamkeit, Verfahren zu ihrer Herstellung, pharmazeutische Präparate, die diese enthalten sowie deren Verwendung zur Herstellung von Arzneimitteln |
EP1177787A3 (en) * | 2000-07-28 | 2003-09-10 | Pfizer Products Inc. | Use of an estrogen agonist/antagonist for treating cataracts |
WO2002089802A2 (en) | 2001-05-08 | 2002-11-14 | Schering Corporation | Use of neurokinin receptor antagonists to treat androgen-dependent diseases |
JP4320252B2 (ja) | 2001-09-06 | 2009-08-26 | シェーリング コーポレイション | アンドロゲン依存性疾患の処置のための1β−ヒドロキシステロイドデヒドロゲナーゼ3型インヒビター |
ES2347643T3 (es) | 2001-10-17 | 2010-11-03 | Schering Corporation | Piperin- y piperazinacetamidas como inhibidores de 17beta hidroxiesteroide deshidrogenasa tipo 3 para el tratamiento de enfermedades dependientes de androgenos. |
US7329654B2 (en) | 2001-12-19 | 2008-02-12 | Janssen Pharmaceutica N.V. | Heteroatom containing tetracyclic derivatives as selective estrogen receptor modulators |
US7105679B2 (en) | 2001-12-19 | 2006-09-12 | Kanojia Ramesh M | Heteroatom containing tetracyclic derivatives as selective estrogen receptor modulators |
WO2003068217A1 (en) * | 2002-02-15 | 2003-08-21 | Endorecherche, Inc. | Biphenil derivatives and their use as antiandrogenic agents |
MY130792A (en) | 2002-11-18 | 2007-07-31 | Schering Corp | 17ß-HYDROXYSTEROID DEHYDROGENASE TYPE 3 INHIBITORS FOR THE TREATMENT OF ANDROGEN DEPENDENT DISEASES |
CN1744930A (zh) | 2002-12-17 | 2006-03-08 | 先灵公司 | 治疗雄激素依赖性疾病的3型17β-羟基类固醇脱氢酶抑制剂 |
US20040224935A1 (en) * | 2003-04-07 | 2004-11-11 | Endorecherche, Inc. | Topical antiandrogenic steroids |
RU2397176C2 (ru) * | 2004-01-07 | 2010-08-20 | Эндорешерш, Инк. | Стероидные фармацевтические продукты, направленные на спираль 12 |
TWI400220B (zh) | 2004-09-13 | 2013-07-01 | Takeda Pharmaceutical | 光活性胺衍生物的製法 |
AU2005297367B2 (en) | 2004-10-20 | 2010-02-04 | Myriel Pharmaceuticals, Llc | Sex steroid precursors alone or in combination with a selective estrogen receptor modulator and/or with estrogens and/or a type 5 CGMP phosphodiesterase inhibitor for the prevention and treatment of vaginal dryness and sexual dysfunction in postmenopausal women |
ES2314747T3 (es) * | 2004-11-18 | 2009-03-16 | Janssen Pharmaceutica Nv | Nuevos derivados de 2h-cromeno como modulares selectivos de receptores de estrogeno. |
GB0513702D0 (en) | 2005-07-04 | 2005-08-10 | Sterix Ltd | Compound |
GB0708376D0 (en) | 2007-05-01 | 2007-06-06 | Alligator Bioscience Ab | Novel polypeptides and uses thereof |
US8268806B2 (en) | 2007-08-10 | 2012-09-18 | Endorecherche, Inc. | Pharmaceutical compositions |
EA017385B1 (ru) | 2007-10-16 | 2012-12-28 | Репрос Терапьютикс Инк. | Применение транс-кломифена для снижения концентрации глюкозы в сыворотке |
GB0722779D0 (en) | 2007-11-20 | 2008-01-02 | Sterix Ltd | Compound |
US20100317635A1 (en) | 2009-06-16 | 2010-12-16 | Endorecherche, Inc. | Treatment of hot flushes, vasomotor symptoms, and night sweats with sex steroid precursors in combination with selective estrogen receptor modulators |
CA2800673A1 (en) * | 2010-06-10 | 2011-12-15 | Aragon Pharmaceuticals, Inc. | Estrogen receptor modulators and uses thereof |
CN107693794A (zh) | 2010-06-16 | 2018-02-16 | 恩多研究公司 | 治疗或预防雌激素相关疾病的方法 |
WO2011159769A2 (en) | 2010-06-17 | 2011-12-22 | Aragon Pharmaceuticals, Inc. | Indane estrogen receptor modulators and uses thereof |
WO2013090829A1 (en) | 2011-12-14 | 2013-06-20 | Aragon Pharmaceuticals, Inc. | Estrogen receptor modulators and uses thereof |
US9018244B2 (en) * | 2011-12-16 | 2015-04-28 | Olema Pharmaceuticals, Inc. | Benzopyran compounds, compositions and uses thereof |
JP2015508825A (ja) | 2012-02-29 | 2015-03-23 | レプロス セラピューティクス インコーポレイティド | アンドロゲン欠乏症を治療するための併用療法 |
WO2014203129A1 (en) | 2013-06-19 | 2014-12-24 | Olema Pharmaceuticals, Inc. | Combinations of benzopyran compounds, compositions and uses thereof |
WO2014203132A1 (en) | 2013-06-19 | 2014-12-24 | Olema Pharmaceuticals, Inc. | Substituted benzopyran compounds, compositions and uses thereof |
AU2014281511A1 (en) | 2013-06-19 | 2015-12-03 | Seragon Pharmaceuticals, Inc. | Estrogen receptor modulator and uses thereof |
US9744177B2 (en) | 2014-03-10 | 2017-08-29 | Endorecherche, Inc. | Treatment of male androgen deficiency symptoms or diseases with sex steroid precursor combined with SERM |
CA2941161A1 (en) * | 2014-03-13 | 2015-09-17 | F.Hoffmann-La Roche Ag | Methods and compositions for modulating estrogen receptor mutants |
CN107406433A (zh) * | 2014-12-18 | 2017-11-28 | 豪夫迈·罗氏有限公司 | 用于治疗癌症的2,3‑二苯基色烯的衍生物 |
US10053451B2 (en) | 2015-05-26 | 2018-08-21 | Genentech, Inc. | Heterocyclic estrogen receptor modulators and uses thereof |
UA122348C2 (uk) | 2015-10-27 | 2020-10-26 | Сан Фарма Адвансед Ресьорч Компані Лімітед | Нові гетероциклічні антиестрогени |
AU2016352592B2 (en) | 2015-11-10 | 2023-04-27 | Paracrine Therapeutics Ab | Treatment of ER-negative breast cancer with an PDGF-CC inhibitor and an anti estrogen |
DK3525774T3 (da) | 2016-10-11 | 2022-03-14 | Univ Duke | Lasofoxifen behandling af er+ brystcancer |
CN112261937B (zh) | 2018-04-10 | 2023-11-14 | 杜克大学 | 乳腺癌的拉索昔芬治疗 |
KR20220046586A (ko) | 2019-07-22 | 2022-04-14 | 썬 파마 어드밴스트 리서치 컴패니 리미티드 | 선택적 에스트로겐 수용체 분해제 |
GB202116903D0 (en) | 2021-11-18 | 2022-01-05 | Sermonix Pharmaceuticals Inc | Lasofoxifene treatment of aromatase-resistant er+ cancer |
Family Cites Families (36)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2875199A (en) * | 1958-04-22 | 1959-02-24 | Searle & Co | Lactones of 17-carboxyalkylated estra-1, 3, 5(10)-triene-3, 17-diols and 3-ethers |
US3396169A (en) * | 1966-10-26 | 1968-08-06 | Upjohn Co | Substituted 2-phenyl-1-(tertiary-aminoalkoxy) phenyl-3, 4-dihydronaphthalenes |
DE1518002C3 (de) * | 1965-01-02 | 1975-01-23 | Merck Patent Gmbh, 6100 Darmstadt | Isoflavane und Isoflavene und Verfahren zu Ihrer Herstellung sowie diese enthaltende Arzneimittel |
US3321483A (en) * | 1966-06-09 | 1967-05-23 | Bristol Myers Co | Substituted 3, 4-dihydro-3-phenyl-4-hydroxy-{[(amino)alkoxy (or alkylthio) phenyl]} thiochroman |
US3995060A (en) * | 1972-06-20 | 1976-11-30 | Schering Corporation | Antiandrogenic agents and method for the treatment of androgen dependent disease states |
US4161540A (en) * | 1966-08-22 | 1979-07-17 | Schering Corporation | Antiandrogenic agents and methods for the treatment of androgen dependent disease states |
US3597431A (en) * | 1969-07-23 | 1971-08-03 | American Cyanamid Co | 1-(4'-substituted-phenyl)-2-(phenyl lower alkyl)-1,2,3,4-tetrahydroisoquinolines |
DE2658307C2 (de) * | 1976-12-22 | 1979-03-15 | Klinge Pharma Gmbh & Co, 8000 Muenchen | Di-O'-hydroxyphenyD-alkanverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
US4213978A (en) * | 1978-12-05 | 1980-07-22 | Interx Research Corporation | Anti-acne and anti-seborrhea prodrug derivatives of progesterone |
FR2465486A1 (fr) * | 1979-09-21 | 1981-03-27 | Roussel Uclaf | Nouvelle application utilisant la lh-rh ou des agonistes |
DE2943107C2 (de) * | 1979-10-25 | 1984-07-26 | Robert 6600 Saarbrücken Langen | Verfahren zum Entrosten |
US5098903A (en) * | 1980-03-07 | 1992-03-24 | Board Of Regents Of The University Of Oklahoma | Diphenylcyclopropyl analogs as antiestrogenic and antitumor agents |
FR2528434B1 (fr) * | 1982-06-11 | 1985-07-19 | Roussel Uclaf | Nouveaux 19-nor steroides substitues en 11b et eventuellement en 2, leur procede de preparation et leur application comme medicament |
GB8311678D0 (en) * | 1983-04-28 | 1983-06-02 | Ici Plc | Phenol derivatives |
JPH0670682B2 (ja) * | 1983-08-19 | 1994-09-07 | 日照技研株式会社 | 照明装置 |
GB8327256D0 (en) * | 1983-10-12 | 1983-11-16 | Ici Plc | Steroid derivatives |
GB8410899D0 (en) * | 1984-04-27 | 1984-06-06 | Ici Plc | Phenol derivatives |
GB8410901D0 (en) * | 1984-04-27 | 1984-06-06 | Ici Plc | Phenol derivatives |
IE58417B1 (en) * | 1984-04-27 | 1993-09-22 | Ici Plc | Chemical derivatives |
US4659695A (en) * | 1985-02-08 | 1987-04-21 | Fernand Labrie | Method of treatment of prostate cancer |
EP0195015B1 (en) * | 1984-08-02 | 1992-05-13 | LABRIE, Fernand | Pharmaceutical composition for combination therapy of hormone dependent cancers |
FR2610933B1 (fr) * | 1987-02-18 | 1989-06-09 | Roussel Uclaf | Nouveaux 19-nor steroides substitues en position 7, leur preparation, leur application comme medicaments, les compositions pharmaceutiques les renfermant |
FR2618783B1 (fr) * | 1987-07-30 | 1991-02-01 | Roussel Uclaf | Nouveaux 17-aryle steroides, leurs procedes et des intermediaires de preparation comme medicaments et les compositions pharmaceutiques les renfermant |
FR2630110B1 (fr) * | 1988-04-13 | 1990-07-27 | Adir | Nouveaux derives heteroarotinoides, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
US5021432A (en) * | 1988-04-26 | 1991-06-04 | Yoshitomi Pharmaceutical Industries, Ltd. | Benzopyran compound and its pharmaceutical use |
US4950684A (en) * | 1988-05-20 | 1990-08-21 | G. D. Searle & Co. | 2,2-di-substituted benzopyran leukotriene-D4 antagonists |
DE3821148A1 (de) * | 1988-06-23 | 1989-12-28 | Erwin Von Dr Angerer | Aminoalkylindole, verfahren zu deren herstellung und diese enthaltende pharmazeutische praeparate |
US5395842A (en) * | 1988-10-31 | 1995-03-07 | Endorecherche Inc. | Anti-estrogenic compounds and compositions |
US5204337A (en) * | 1988-10-31 | 1993-04-20 | Endorecherche Inc. | Estrogen nucleus derivatives for use in inhibition of sex steroid activity |
HU221589B (hu) * | 1989-03-10 | 2002-11-28 | Endorecherche Inc. | Emlő- és méhrák kezelésére alkalmas kombinációs gyógyszerkészítmény és eljárás előállítására |
US4963568A (en) * | 1989-05-31 | 1990-10-16 | Abbott Laboratories | Dopamine agonists |
EP0528975A4 (en) * | 1990-05-17 | 1993-09-15 | Baylor College Of Medicine | Growth inhibitors and methods of treating cancer and cell proliferative diseases |
DE69023906T2 (de) * | 1990-08-09 | 1996-04-11 | Council Scient Ind Res | Benzopyrane und Verfahren zu deren Herstellung. |
DE4117512A1 (de) * | 1991-05-25 | 1992-11-26 | Schering Ag | 2-phenylbenzo(b)furane und -thiophene, verfahren zu deren herstellung und diese enthaltende pharmazeutische praeparate |
US5407947A (en) * | 1993-11-05 | 1995-04-18 | Eli Lilly And Company | Methods for inhibiting bone loss using pyrolidine and piperidine substituted benzopyrans |
US5446061A (en) * | 1993-11-05 | 1995-08-29 | Eli Lilly And Company | Methods for lowering serum cholesterol |
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