MXPA02003884A - Metodos de sintetizar asimetricamente enantiomeros de casodex, sus derivados e intermediarios de los mismos. - Google Patents
Metodos de sintetizar asimetricamente enantiomeros de casodex, sus derivados e intermediarios de los mismos.Info
- Publication number
- MXPA02003884A MXPA02003884A MXPA02003884A MXPA02003884A MXPA02003884A MX PA02003884 A MXPA02003884 A MX PA02003884A MX PA02003884 A MXPA02003884 A MX PA02003884A MX PA02003884 A MXPA02003884 A MX PA02003884A MX PA02003884 A MXPA02003884 A MX PA02003884A
- Authority
- MX
- Mexico
- Prior art keywords
- compound
- formula
- derivatives
- casodexreg
- acylanalides
- Prior art date
Links
- 230000002194 synthesizing effect Effects 0.000 title abstract 3
- 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 title abstract 2
- LKJPYSCBVHEWIU-UHFFFAOYSA-N N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C(O)(C)CS(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-UHFFFAOYSA-N 0.000 title 1
- 229940097647 casodex Drugs 0.000 title 1
- 239000000543 intermediate Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 5
- LKJPYSCBVHEWIU-KRWDZBQOSA-N (R)-bicalutamide Chemical compound C([C@@](O)(C)C(=O)NC=1C=C(C(C#N)=CC=1)C(F)(F)F)S(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-KRWDZBQOSA-N 0.000 abstract 3
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 3
- 229960000997 bicalutamide Drugs 0.000 abstract 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 229910052717 sulfur Inorganic materials 0.000 abstract 2
- 239000011593 sulfur Chemical group 0.000 abstract 2
- OKIHXNKYYGUVTE-UHFFFAOYSA-N 4-Fluorothiophenol Chemical compound FC1=CC=C(S)C=C1 OKIHXNKYYGUVTE-UHFFFAOYSA-N 0.000 abstract 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 abstract 1
- XFTRTWQBIOMVPK-YFKPBYRVSA-N Citramalic acid Natural products OC(=O)[C@](O)(C)CC(O)=O XFTRTWQBIOMVPK-YFKPBYRVSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000005277 alkyl imino group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- XFTRTWQBIOMVPK-UHFFFAOYSA-N citramalic acid Chemical compound OC(=O)C(O)(C)CC(O)=O XFTRTWQBIOMVPK-UHFFFAOYSA-N 0.000 abstract 1
- 125000001841 imino group Chemical group [H]N=* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- -1 sulphinyl Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/02—Preparation of sulfones; Preparation of sulfoxides by formation of sulfone or sulfoxide groups by oxidation of sulfides, or by formation of sulfone groups by oxidation of sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D317/34—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16041299P | 1999-10-19 | 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 (1)
| Publication Number | Publication Date |
|---|---|
| MXPA02003884A true MXPA02003884A (es) | 2004-09-06 |
Family
ID=22576803
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA02003884A MXPA02003884A (es) | 1999-10-19 | 2000-10-18 | Metodos de sintetizar asimetricamente enantiomeros de casodex, sus derivados e intermediarios de los mismos. |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US6583306B1 (https=) |
| EP (1) | EP1222165A2 (https=) |
| JP (1) | JP5112583B2 (https=) |
| KR (1) | KR20020091047A (https=) |
| CN (1) | CN1409702A (https=) |
| AU (1) | AU1968601A (https=) |
| BR (1) | BR0014889A (https=) |
| CA (1) | CA2387570A1 (https=) |
| CZ (1) | CZ20021340A3 (https=) |
| HK (1) | HK1048298A1 (https=) |
| HU (1) | HUP0203785A2 (https=) |
| IL (2) | IL149056A0 (https=) |
| MX (1) | MXPA02003884A (https=) |
| NO (1) | NO20021831L (https=) |
| NZ (1) | NZ518392A (https=) |
| PL (1) | PL354620A1 (https=) |
| WO (1) | WO2001028990A2 (https=) |
| ZA (1) | ZA200202947B (https=) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US7759520B2 (en) | 1996-11-27 | 2010-07-20 | University Of Tennessee Research Foundation | Synthesis of selective androgen receptor modulators |
| US8445534B2 (en) | 2000-08-24 | 2013-05-21 | University Of Tennessee Research Foundation | Treating androgen decline in aging male (ADAM)-associated conditions with SARMs |
| US6838484B2 (en) | 2000-08-24 | 2005-01-04 | University Of Tennessee Research Foundation | Formulations comprising selective androgen receptor modulators |
| 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 |
| US7026500B2 (en) | 2000-08-24 | 2006-04-11 | University Of Tennessee Research Foundation | Halogenated selective androgen receptor modulators and methods of use thereof |
| US6998500B2 (en) | 2000-08-24 | 2006-02-14 | University Of Tennessee Research Foundation | Selective androgen receptor modulators and methods of use thereof |
| EP1406855A4 (en) * | 2001-06-13 | 2006-04-19 | Teva Gyogyszergyar Reszvenytar | NOVEL PROCESS FOR THE PREPARATION OF RAC-BICALUTAMIDE AND INTERMEDIATE PRODUCTS THEREOF |
| US8853266B2 (en) | 2001-12-06 | 2014-10-07 | University Of Tennessee Research Foundation | Selective androgen receptor modulators for treating diabetes |
| DK1463497T3 (da) | 2001-12-06 | 2012-01-30 | Gtx Inc | Behandling af muskelsvind med selektive androgenreceptormodulatorer |
| NZ533943A (en) * | 2001-12-13 | 2006-06-30 | Sumitomo Chemical Co | Crystal of bicalutamide and production method thereof |
| CA2475108A1 (en) | 2002-02-07 | 2003-08-14 | Mitchell S. Steiner | Treating benign prostate hyperplasia with sarms |
| US7705182B2 (en) | 2002-02-28 | 2010-04-27 | University Of Tennessee Research Foundation | Multi-substituted selective androgen receptor modulators and methods of use thereof |
| US7772433B2 (en) | 2002-02-28 | 2010-08-10 | University Of Tennessee Research Foundation | SARMS and method of use thereof |
| 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 |
| 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 |
| JP2005529952A (ja) | 2002-06-17 | 2005-10-06 | 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 | Ｎ架橋選択的アンドロゲン受容体修飾物質及びその使用方法 |
| US7741371B2 (en) | 2002-06-17 | 2010-06-22 | University Of Tennessee Research Foundation | Selective androgen receptor modulators and methods of use thereof |
| EP1402924B1 (de) * | 2002-09-04 | 2008-12-31 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | 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 |
| CA2502209A1 (en) | 2002-10-15 | 2004-04-29 | University Of Tennessee Research Foundation | Methylene-bridged selective androgen receptor modulators and methods of use thereof |
| 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 |
| WO2005060647A2 (en) | 2003-12-16 | 2005-07-07 | Gtx, Inc. | Prodrugs of selective androgen receptor modulators 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 |
| US9884038B2 (en) | 2004-06-07 | 2018-02-06 | University Of Tennessee Research Foundation | Selective androgen receptor modulator and methods of use thereof |
| US7550505B2 (en) * | 2006-07-24 | 2009-06-23 | 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 |
| ES2581765T3 (es) | 2006-08-24 | 2016-09-07 | University Of Tennessee Research Foundation | Acilanilidas sustituidas y métodos de uso de las mismas |
| US7968603B2 (en) | 2007-09-11 | 2011-06-28 | University Of Tennessee Research Foundation | Solid forms of selective androgen receptor modulators |
| ITBO20090236A1 (it) * | 2009-04-10 | 2010-10-11 | Consiglio Nazionale Ricerche | Procedimento per la sintesi di composti per il trattamento del tumore alla prostata |
| WO2010116342A2 (en) * | 2009-04-10 | 2010-10-14 | Consiglio Nazionale Delle Ricerche | Non-steroidal compounds for androgen receptor modulation |
| US8450374B2 (en) * | 2009-06-29 | 2013-05-28 | 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 |
| LT2872482T (lt) | 2012-07-13 | 2020-12-28 | Oncternal Therapeutics, Inc. | Krūties vėžių gydymo būdas selektyviu androgeno receptoriaus moduliatoriumi |
| 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) |
| 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) |
| 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) |
| 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) |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE28864T1 (de) * | 1982-07-23 | 1987-08-15 | Ici Plc | Amide-derivate. |
| GB8617652D0 (en) | 1986-07-18 | 1986-08-28 | Ici Plc | Acylanilide derivatives |
| AU1687395A (en) * | 1994-01-21 | 1995-08-08 | Sepracor, Inc. | Methods and compositions for treating androgen-dependent diseases using optically pure r-(-)-casodex |
| WO1998055153A1 (en) | 1997-06-04 | 1998-12-10 | The University Of Tennessee Research Corporation | 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 HU HU0203785A patent/HUP0203785A2/hu unknown
- 2000-10-18 HK HK03100367.2A patent/HK1048298A1/zh unknown
- 2000-10-18 CN CN00817022A patent/CN1409702A/zh active Pending
- 2000-10-18 WO PCT/US2000/041233 patent/WO2001028990A2/en not_active Ceased
- 2000-10-18 CZ CZ20021340A patent/CZ20021340A3/cs unknown
- 2000-10-18 AU AU19686/01A patent/AU1968601A/en not_active Abandoned
- 2000-10-18 US US09/691,621 patent/US6583306B1/en not_active Expired - Lifetime
- 2000-10-18 NZ NZ518392A patent/NZ518392A/en unknown
- 2000-10-18 EP EP00982690A patent/EP1222165A2/en not_active Withdrawn
- 2000-10-18 KR KR1020027004966A patent/KR20020091047A/ko not_active Withdrawn
- 2000-10-18 PL PL00354620A patent/PL354620A1/xx not_active Application Discontinuation
- 2000-10-18 CA CA002387570A patent/CA2387570A1/en not_active Abandoned
- 2000-10-18 MX MXPA02003884A patent/MXPA02003884A/es active IP Right Grant
- 2000-10-18 IL IL14905600A patent/IL149056A0/xx unknown
- 2000-10-18 JP JP2001531790A patent/JP5112583B2/ja not_active Expired - Fee Related
- 2000-10-18 BR BR0014889-0A patent/BR0014889A/pt 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
Also Published As
| Publication number | Publication date |
|---|---|
| WO2001028990A2 (en) | 2001-04-26 |
| CA2387570A1 (en) | 2001-04-26 |
| EP1222165A2 (en) | 2002-07-17 |
| US20040030130A1 (en) | 2004-02-12 |
| IL149056A (en) | 2011-05-31 |
| IL149056A0 (en) | 2002-11-10 |
| JP2003512351A (ja) | 2003-04-02 |
| BR0014889A (pt) | 2002-12-31 |
| NO20021831L (no) | 2002-06-19 |
| WO2001028990A3 (en) | 2001-09-07 |
| HUP0203785A2 (hu) | 2003-04-28 |
| ZA200202947B (en) | 2003-09-23 |
| US6583306B1 (en) | 2003-06-24 |
| KR20020091047A (ko) | 2002-12-05 |
| JP5112583B2 (ja) | 2013-01-09 |
| CN1409702A (zh) | 2003-04-09 |
| CZ20021340A3 (cs) | 2002-08-14 |
| AU1968601A (en) | 2001-04-30 |
| NO20021831D0 (no) | 2002-04-18 |
| US7022869B2 (en) | 2006-04-04 |
| PL354620A1 (en) | 2004-02-09 |
| NZ518392A (en) | 2004-02-27 |
| HK1048298A1 (zh) | 2003-03-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG | Grant or registration | ||
| GB | Transfer or rights |