JP2003512351A5 - - Google Patents
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- Publication number
- JP2003512351A5 JP2003512351A5 JP2001531790A JP2001531790A JP2003512351A5 JP 2003512351 A5 JP2003512351 A5 JP 2003512351A5 JP 2001531790 A JP2001531790 A JP 2001531790A JP 2001531790 A JP2001531790 A JP 2001531790A JP 2003512351 A5 JP2003512351 A5 JP 2003512351A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- condensation reaction
- alkyl
- citramalic acid
- undergoing
- 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 description 6
- XFTRTWQBIOMVPK-YFKPBYRVSA-N Citramalic acid Natural products OC(=O)[C@](O)(C)CC(O)=O XFTRTWQBIOMVPK-YFKPBYRVSA-N 0.000 description 4
- XFTRTWQBIOMVPK-UHFFFAOYSA-N citramalic acid Chemical compound OC(=O)C(O)(C)CC(O)=O XFTRTWQBIOMVPK-UHFFFAOYSA-N 0.000 description 4
- 238000006482 condensation reaction Methods 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 2
- 0 CC1(CC(O)=O)OC(*)(*)OC1=O Chemical compound CC1(CC(O)=O)OC(*)(*)OC1=O 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16041299P | 1999-10-19 | 1999-10-19 | |
| US60/160,412 | 1999-10-19 | ||
| PCT/US2000/041233 WO2001028990A2 (en) | 1999-10-19 | 2000-10-18 | Methods of asymmetrically synthesizing enantiomers of casodex, its derivatives and intermediates thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003512351A JP2003512351A (ja) | 2003-04-02 |
| JP2003512351A5 true JP2003512351A5 (enExample) | 2007-11-29 |
| JP5112583B2 JP5112583B2 (ja) | 2013-01-09 |
Family
ID=22576803
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001531790A Expired - Fee Related JP5112583B2 (ja) | 1999-10-19 | 2000-10-18 | カソデックス、その誘導体およびその中間体の鏡像体を非対照的に合成する方法 |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US6583306B1 (enExample) |
| EP (1) | EP1222165A2 (enExample) |
| JP (1) | JP5112583B2 (enExample) |
| KR (1) | KR20020091047A (enExample) |
| CN (1) | CN1409702A (enExample) |
| AU (1) | AU1968601A (enExample) |
| BR (1) | BR0014889A (enExample) |
| CA (1) | CA2387570A1 (enExample) |
| CZ (1) | CZ20021340A3 (enExample) |
| HK (1) | HK1048298A1 (enExample) |
| HU (1) | HUP0203785A2 (enExample) |
| IL (2) | IL149056A0 (enExample) |
| MX (1) | MXPA02003884A (enExample) |
| NO (1) | NO20021831L (enExample) |
| NZ (1) | NZ518392A (enExample) |
| PL (1) | PL354620A1 (enExample) |
| WO (1) | WO2001028990A2 (enExample) |
| ZA (1) | ZA200202947B (enExample) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7759520B2 (en) | 1996-11-27 | 2010-07-20 | University Of Tennessee Research Foundation | Synthesis of selective androgen receptor modulators |
| US6995284B2 (en) | 2000-08-24 | 2006-02-07 | The University Of Tennessee Research Foundation | Synthesis of selective androgen receptor modulators |
| US6071957A (en) | 1996-11-27 | 2000-06-06 | The University Of Tennessee Research Corporation | Irreversible non-steroidal antagonist compound and its use in the treatment of prostate cancer |
| US6998500B2 (en) | 2000-08-24 | 2006-02-14 | University Of Tennessee Research Foundation | Selective androgen receptor modulators and methods of use thereof |
| US7026500B2 (en) | 2000-08-24 | 2006-04-11 | University Of Tennessee Research Foundation | Halogenated selective androgen receptor modulators and methods of use thereof |
| US8445534B2 (en) | 2000-08-24 | 2013-05-21 | University Of Tennessee Research Foundation | Treating androgen decline in aging male (ADAM)-associated conditions with SARMs |
| US7622503B2 (en) | 2000-08-24 | 2009-11-24 | University Of Tennessee Research Foundation | Selective androgen receptor modulators and methods of use thereof |
| US8008348B2 (en) | 2001-12-06 | 2011-08-30 | University Of Tennessee Research Foundation | Treating muscle wasting with selective androgen receptor modulators |
| US6838484B2 (en) | 2000-08-24 | 2005-01-04 | University Of Tennessee Research Foundation | Formulations comprising selective androgen receptor modulators |
| EP1406855A4 (en) * | 2001-06-13 | 2006-04-19 | Teva Gyogyszergyar Reszvenytar | NOVEL PROCESS FOR THE PREPARATION OF RAC-BICALUTAMIDE AND INTERMEDIATE PRODUCTS THEREOF |
| CA2469340A1 (en) | 2001-12-06 | 2003-06-19 | Gtx Inc. | Treating muscle wasting with selective androgen receptor modulators |
| US8853266B2 (en) | 2001-12-06 | 2014-10-07 | University Of Tennessee Research Foundation | Selective androgen receptor modulators for treating diabetes |
| KR100938188B1 (ko) * | 2001-12-13 | 2010-01-21 | 스미또모 가가꾸 가부시키가이샤 | 비칼루타미드의 결정 및 그 제조 방법 |
| KR20100112659A (ko) | 2002-02-07 | 2010-10-19 | 지티엑스, 인코포레이티드 | 선택적 안드로겐 수용체 조절자를 이용한 양성 전립선 과형성증의 치료 방법 |
| AU2003217304A1 (en) | 2002-02-28 | 2003-09-16 | The University Of Tennessee Research Corporation | Radiolabeled selective androgen receptor modulators and their use in prostate cancer imaging and therapy |
| KR20040101251A (ko) | 2002-02-28 | 2004-12-02 | 유니버시티 오브 테네시 리서치 파운데이션 | 다치환된 선택적 안드로겐 수용체 모듈레이터 및 이를사용하는 방법 |
| US7772433B2 (en) | 2002-02-28 | 2010-08-10 | University Of Tennessee Research Foundation | SARMS and method of use thereof |
| US7803970B2 (en) | 2002-02-28 | 2010-09-28 | University Of Tennessee Research Foundation | Multi-substitued selective androgen receptor modulators and methods of use thereof |
| DE10222104A1 (de) | 2002-05-17 | 2003-12-04 | Helm Ag | Verfahren zur Herstellung von N-(4'-Cyano-3'-trifluormethyl)-3-(4"-fluorphenylsulfonyl)-2-hydroxy-2-methylpropionamid |
| US7741371B2 (en) | 2002-06-17 | 2010-06-22 | University Of Tennessee Research Foundation | Selective androgen receptor modulators and methods of use thereof |
| HRP20050038A2 (en) | 2002-06-17 | 2005-08-31 | University Of Tennessee Research Foundation | N-bridged selective androgen receptor modulators and methods of use thereof |
| ATE419037T1 (de) * | 2002-09-04 | 2009-01-15 | Fraunhofer Ges Forschung | Verwendung eines mittel zur therapie der herzhypertrophie |
| US20040063782A1 (en) * | 2002-09-27 | 2004-04-01 | Westheim Raymond J.H. | Bicalutamide forms |
| US6818766B2 (en) | 2002-10-02 | 2004-11-16 | Synthon Bv | Process for making bicalutamide and intermediates thereof |
| JP2006506369A (ja) | 2002-10-15 | 2006-02-23 | ユニバーシティ・オブ・テネシー・リサーチ・ファウンデーション | メチレン架橋選択的アンドロゲン受容体調節剤及びその使用方法 |
| US8309603B2 (en) | 2004-06-07 | 2012-11-13 | University Of Tennessee Research Foundation | SARMs and method of use thereof |
| JP4322621B2 (ja) | 2003-10-16 | 2009-09-02 | 住友化学株式会社 | 4’−シアノ−3−[(4−フルオロフェニル)スルホニル]−2−ヒドロキシ−2−メチル−3’−トリフルオロメチルプロピオンアニリドの製造方法 |
| EA200501761A1 (ru) | 2003-12-16 | 2006-04-28 | Джи Ти Икс, ИНК. | Пролекарственные формы селективных модуляторов андрогеновых рецепторов и способы их применения |
| US9884038B2 (en) | 2004-06-07 | 2018-02-06 | University Of Tennessee Research Foundation | Selective androgen receptor modulator and methods of use thereof |
| US9889110B2 (en) | 2004-06-07 | 2018-02-13 | University Of Tennessee Research Foundation | Selective androgen receptor modulator for treating hormone-related conditions |
| WO2008013791A2 (en) * | 2006-07-24 | 2008-01-31 | University Of Delaware | Pan-antagonists for the androgen receptor and androgen receptor mutants associated with anti-androgen withdrawal |
| US9844528B2 (en) | 2006-08-24 | 2017-12-19 | University Of Tennessee Research Foundation | SARMs and method of use thereof |
| US9730908B2 (en) | 2006-08-24 | 2017-08-15 | University Of Tennessee Research Foundation | SARMs and method of use thereof |
| US10010521B2 (en) | 2006-08-24 | 2018-07-03 | University Of Tennessee Research Foundation | SARMs and method of use thereof |
| CN101528214B (zh) | 2006-08-24 | 2013-06-05 | 田纳西大学研究基金会 | 取代的n-酰基苯胺及其使用方法 |
| US7968603B2 (en) | 2007-09-11 | 2011-06-28 | University Of Tennessee Research Foundation | Solid forms of selective androgen receptor modulators |
| US8741951B2 (en) | 2009-04-10 | 2014-06-03 | CNR—Consiglio Nazionale Delle Ricerche | Non-steroidal compounds for androgen receptor modulation |
| ITBO20090236A1 (it) * | 2009-04-10 | 2010-10-11 | Consiglio Nazionale Ricerche | Procedimento per la sintesi di composti per il trattamento del tumore alla prostata |
| WO2011008543A2 (en) * | 2009-06-29 | 2011-01-20 | University Of Delaware | Pan-antagonists for the androgen receptor and androgen receptor mutants associated with anti-androgen withdrawal |
| CN103539710A (zh) * | 2012-07-02 | 2014-01-29 | 国药一心制药有限公司 | 一种(r)-比卡鲁胺的合成方法 |
| US9622992B2 (en) | 2012-07-13 | 2017-04-18 | Gtx, Inc. | Method of treating androgen receptor (AR)-positive breast cancers with selective androgen receptor modulator (SARMs) |
| US10314807B2 (en) | 2012-07-13 | 2019-06-11 | Gtx, Inc. | Method of treating HER2-positive breast cancers with selective androgen receptor modulators (SARMS) |
| US9744149B2 (en) | 2012-07-13 | 2017-08-29 | Gtx, Inc. | Method of treating androgen receptor (AR)-positive breast cancers with selective androgen receptor modulator (SARMs) |
| PL2872482T3 (pl) | 2012-07-13 | 2021-03-08 | Oncternal Therapeutics, Inc. | Sposób leczenia raków sutka z użyciem selektywnego modulatora receptora androgenowego (sarm) |
| US9969683B2 (en) | 2012-07-13 | 2018-05-15 | Gtx, Inc. | Method of treating estrogen receptor (ER)-positive breast cancers with selective androgen receptor modulator (SARMS) |
| US10258596B2 (en) | 2012-07-13 | 2019-04-16 | Gtx, Inc. | Method of treating HER2-positive breast cancers with selective androgen receptor modulators (SARMS) |
| US10987334B2 (en) | 2012-07-13 | 2021-04-27 | University Of Tennessee Research Foundation | Method of treating ER mutant expressing breast cancers with selective androgen receptor modulators (SARMs) |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU88769I2 (fr) * | 1982-07-23 | 1996-11-05 | Zeneca Ltd | Bicalutamide et ses sels et esters pharmaceutiquement acceptables (Casodex (R)) |
| GB8617652D0 (en) | 1986-07-18 | 1986-08-28 | Ici Plc | Acylanilide derivatives |
| JPH09508125A (ja) * | 1994-01-21 | 1997-08-19 | セプラコー,インコーポレイテッド | 光学的純正r−(−)−カソデックスを使用した男性ホルモン依存疾患治療のための方法と組成 |
| AU7723198A (en) | 1997-06-04 | 1998-12-21 | University Of Tennessee Research Corporation, The | Non-steroidal radiolabeled agonist/antagonist compounds and their use in prostate cancer imaging |
| US6186674B1 (en) * | 1998-09-15 | 2001-02-13 | Lucent Technologies, Inc. | Optical sub-assembly package mount |
| US6252762B1 (en) * | 1999-04-21 | 2001-06-26 | Telcordia Technologies, Inc. | Rechargeable hybrid battery/supercapacitor system |
| US6331992B1 (en) * | 2000-04-07 | 2001-12-18 | Stratos Lightwave, Inc. | Small format optical subassembly |
| AU2002231027A1 (en) * | 2000-12-13 | 2002-06-24 | Teraconnect, Inc. | A packaging system for two-dimensional optoelectronic arrays |
| US6821032B2 (en) * | 2002-05-28 | 2004-11-23 | Intel Corporation | Methods of sealing electronic, optical and electro-optical packages and related package and substrate designs |
-
2000
- 2000-10-18 US US09/691,621 patent/US6583306B1/en not_active Expired - Lifetime
- 2000-10-18 IL IL14905600A patent/IL149056A0/xx unknown
- 2000-10-18 MX MXPA02003884A patent/MXPA02003884A/es active IP Right Grant
- 2000-10-18 AU AU19686/01A patent/AU1968601A/en not_active Abandoned
- 2000-10-18 CA CA002387570A patent/CA2387570A1/en not_active Abandoned
- 2000-10-18 WO PCT/US2000/041233 patent/WO2001028990A2/en not_active Ceased
- 2000-10-18 KR KR1020027004966A patent/KR20020091047A/ko not_active Withdrawn
- 2000-10-18 JP JP2001531790A patent/JP5112583B2/ja not_active Expired - Fee Related
- 2000-10-18 CZ CZ20021340A patent/CZ20021340A3/cs unknown
- 2000-10-18 NZ NZ518392A patent/NZ518392A/en unknown
- 2000-10-18 CN CN00817022A patent/CN1409702A/zh active Pending
- 2000-10-18 EP EP00982690A patent/EP1222165A2/en not_active Withdrawn
- 2000-10-18 HU HU0203785A patent/HUP0203785A2/hu unknown
- 2000-10-18 BR BR0014889-0A patent/BR0014889A/pt not_active Application Discontinuation
- 2000-10-18 HK HK03100367.2A patent/HK1048298A1/zh unknown
- 2000-10-18 PL PL00354620A patent/PL354620A1/xx not_active Application Discontinuation
-
2002
- 2002-04-09 IL IL149056A patent/IL149056A/en not_active IP Right Cessation
- 2002-04-15 ZA ZA200202947A patent/ZA200202947B/xx unknown
- 2002-04-18 NO NO20021831A patent/NO20021831L/no not_active Application Discontinuation
-
2003
- 2003-05-23 US US10/444,343 patent/US7022869B2/en not_active Expired - Fee Related
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