BR0014889A - Métodos para assimetricamente sintetizar um enanciÈmero de uma acilanilida ou um seu derivado, para tratar câncer de próstata, para formar um composto opticamente ativo e para sintetizar um composto opticamente ativo, e, composto - Google Patents
Métodos para assimetricamente sintetizar um enanciÈmero de uma acilanilida ou um seu derivado, para tratar câncer de próstata, para formar um composto opticamente ativo e para sintetizar um composto opticamente ativo, e, compostoInfo
- Publication number
- BR0014889A BR0014889A BR0014889-0A BR0014889A BR0014889A BR 0014889 A BR0014889 A BR 0014889A BR 0014889 A BR0014889 A BR 0014889A BR 0014889 A BR0014889 A BR 0014889A
- Authority
- BR
- Brazil
- Prior art keywords
- compound
- optically active
- active compound
- formula
- methods
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 11
- 230000002194 synthesizing effect Effects 0.000 title abstract 4
- 206010060862 Prostate cancer Diseases 0.000 title abstract 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 title abstract 2
- -1 and Chemical class 0.000 title abstract 2
- 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
- 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 abstract 3
- 229960000997 bicalutamide Drugs 0.000 abstract 3
- 229940097647 casodex Drugs 0.000 abstract 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 abstract 2
- 229910052717 sulfur Inorganic materials 0.000 abstract 2
- 239000011593 sulfur Substances 0.000 abstract 2
- OKIHXNKYYGUVTE-UHFFFAOYSA-N 4-Fluorothiophenol Chemical group 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
- 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 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 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 compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 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
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 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)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (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 |
|---|---|
| BR0014889A true BR0014889A (pt) | 2002-12-31 |
Family
ID=22576803
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR0014889-0A BR0014889A (pt) | 1999-10-19 | 2000-10-18 | Métodos para assimetricamente sintetizar um enanciÈmero de uma acilanilida ou um seu derivado, para tratar câncer de próstata, para formar um composto opticamente ativo e para sintetizar um composto opticamente ativo, e, composto |
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 |
| US7759520B2 (en) | 1996-11-27 | 2010-07-20 | 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 |
| US7622503B2 (en) | 2000-08-24 | 2009-11-24 | University Of Tennessee Research Foundation | Selective androgen receptor modulators and methods of use thereof |
| US7547728B2 (en) | 2001-12-06 | 2009-06-16 | University Of Tennessee Research Foundation | Treating muscle wasting with 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 |
| US7253210B2 (en) | 2002-10-15 | 2007-08-07 | University Of Tennessee Research Foundation | Methylene-bridged 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 |
| US6838484B2 (en) | 2000-08-24 | 2005-01-04 | University Of Tennessee Research Foundation | Formulations comprising 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 |
| US8008348B2 (en) | 2001-12-06 | 2011-08-30 | University Of Tennessee Research Foundation | Treating muscle wasting with selective androgen receptor modulators |
| WO2002100339A2 (en) * | 2001-06-13 | 2002-12-19 | Biogal Gyogyszergyar Rt. | Novel process for preparing rac-bicalutamide and its intermediates |
| US8853266B2 (en) | 2001-12-06 | 2014-10-07 | University Of Tennessee Research Foundation | Selective androgen receptor modulators for treating diabetes |
| CN1602299A (zh) * | 2001-12-13 | 2005-03-30 | 住友化学工业株式会社 | 比卡鲁胺晶体及其制造方法 |
| PT1480634E (pt) | 2002-02-07 | 2011-10-12 | Univ Tennessee Res Foundation | Moduladores selectivos do receptor do androgénio (sarms) para o tratamento da hiperplasia benigna da próstata |
| 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 |
| US7344700B2 (en) | 2002-02-28 | 2008-03-18 | University Of Tennessee Research Corporation | Radiolabeled selective androgen receptor modulators and their use in prostate cancer imaging and therapy |
| EP1487458B1 (en) | 2002-02-28 | 2011-11-16 | University Of Tennessee Research Foundation | Multi-substituted 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 |
| GEP20074191B (en) | 2002-06-17 | 2007-09-10 | Univ Tennessee Res Foundation | N-bridged selective androgen receptor modulators and methods of use thereof |
| DE50213170D1 (de) * | 2002-09-04 | 2009-02-12 | 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 |
| 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 |
| CA2522874A1 (en) | 2003-12-16 | 2005-07-07 | Gtx, Inc. | Prodrugs of selective androgen receptor modulators and methods of use thereof |
| 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 |
| US9730908B2 (en) | 2006-08-24 | 2017-08-15 | University Of Tennessee Research Foundation | SARMs and method of use thereof |
| US9844528B2 (en) | 2006-08-24 | 2017-12-19 | 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 |
| US10010521B2 (en) | 2006-08-24 | 2018-07-03 | University Of Tennessee Research Foundation | SARMs and method of use thereof |
| 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 |
| 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 |
| 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) |
| 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) |
| 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) |
| PT2872482T (pt) | 2012-07-13 | 2020-09-22 | Oncternal Therapeutics Inc | Método de tratamento de cancro de mama com modulador seletivo do recetor de andrógeno (sarm) |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0100172B1 (en) | 1982-07-23 | 1987-08-12 | Imperial Chemical Industries Plc | Amide derivatives |
| GB8617652D0 (en) | 1986-07-18 | 1986-08-28 | Ici Plc | Acylanilide derivatives |
| CA2181358A1 (en) * | 1994-01-21 | 1995-07-27 | Nancy M. Gray | 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 PL PL00354620A patent/PL354620A1/xx not_active Application Discontinuation
- 2000-10-18 NZ NZ518392A patent/NZ518392A/en unknown
- 2000-10-18 KR KR1020027004966A patent/KR20020091047A/ko not_active Withdrawn
- 2000-10-18 EP EP00982690A patent/EP1222165A2/en not_active Withdrawn
- 2000-10-18 US US09/691,621 patent/US6583306B1/en not_active Expired - Lifetime
- 2000-10-18 WO PCT/US2000/041233 patent/WO2001028990A2/en not_active Ceased
- 2000-10-18 HK HK03100367.2A patent/HK1048298A1/zh unknown
- 2000-10-18 BR BR0014889-0A patent/BR0014889A/pt not_active Application Discontinuation
- 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 JP JP2001531790A patent/JP5112583B2/ja not_active Expired - Fee Related
- 2000-10-18 CZ CZ20021340A patent/CZ20021340A3/cs unknown
- 2000-10-18 CA CA002387570A patent/CA2387570A1/en not_active Abandoned
- 2000-10-18 IL IL14905600A patent/IL149056A0/xx unknown
- 2000-10-18 HU HU0203785A patent/HUP0203785A2/hu unknown
- 2000-10-18 CN CN00817022A patent/CN1409702A/zh active Pending
-
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 |
|---|---|
| JP5112583B2 (ja) | 2013-01-09 |
| CZ20021340A3 (cs) | 2002-08-14 |
| CA2387570A1 (en) | 2001-04-26 |
| CN1409702A (zh) | 2003-04-09 |
| ZA200202947B (en) | 2003-09-23 |
| NO20021831D0 (no) | 2002-04-18 |
| IL149056A0 (en) | 2002-11-10 |
| US7022869B2 (en) | 2006-04-04 |
| US20040030130A1 (en) | 2004-02-12 |
| EP1222165A2 (en) | 2002-07-17 |
| NO20021831L (no) | 2002-06-19 |
| NZ518392A (en) | 2004-02-27 |
| PL354620A1 (en) | 2004-02-09 |
| HUP0203785A2 (hu) | 2003-04-28 |
| WO2001028990A2 (en) | 2001-04-26 |
| MXPA02003884A (es) | 2004-09-06 |
| IL149056A (en) | 2011-05-31 |
| HK1048298A1 (zh) | 2003-03-28 |
| AU1968601A (en) | 2001-04-30 |
| US6583306B1 (en) | 2003-06-24 |
| KR20020091047A (ko) | 2002-12-05 |
| JP2003512351A (ja) | 2003-04-02 |
| WO2001028990A3 (en) | 2001-09-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B11A | Dismissal acc. art.33 of ipl - examination not requested within 36 months of filing | ||
| B11Y | Definitive dismissal - extension of time limit for request of examination expired [chapter 11.1.1 patent gazette] |