JP2003513955A5 - - Google Patents
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- Publication number
- JP2003513955A5 JP2003513955A5 JP2001536512A JP2001536512A JP2003513955A5 JP 2003513955 A5 JP2003513955 A5 JP 2003513955A5 JP 2001536512 A JP2001536512 A JP 2001536512A JP 2001536512 A JP2001536512 A JP 2001536512A JP 2003513955 A5 JP2003513955 A5 JP 2003513955A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- carbon atoms
- intermediate compound
- substantially pure
- cyano
- 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
- 125000000217 alkyl group Chemical group 0.000 description 19
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- -1 nitro, carboxy, carbamoyl Chemical group 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 8
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 8
- 125000004414 alkyl thio group Chemical group 0.000 description 8
- 125000004093 cyano group Chemical group *C#N 0.000 description 8
- 229910052717 sulfur Inorganic materials 0.000 description 8
- 239000011593 sulfur Substances 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 7
- 125000001589 carboacyl group Chemical group 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- KMPWYEUPVWOPIM-KODHJQJWSA-N cinchonidine Chemical compound C1=CC=C2C([C@H]([C@H]3[N@]4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-KODHJQJWSA-N 0.000 description 4
- KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 125000001841 imino group Chemical group [H]N=* 0.000 description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 4
- 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 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 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 description 3
- 125000005118 N-alkylcarbamoyl group Chemical group 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 230000001548 androgenic effect Effects 0.000 description 3
- 229960000997 bicalutamide Drugs 0.000 description 3
- 229940097647 casodex Drugs 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000005277 alkyl imino group Chemical group 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16188499P | 1999-10-27 | 1999-10-27 | |
| US60/161,884 | 1999-10-27 | ||
| PCT/US2000/041609 WO2001034563A1 (en) | 1999-10-27 | 2000-10-25 | Resolution of intermediates in the synthesis of substantially pure bicalutamide |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003513955A JP2003513955A (ja) | 2003-04-15 |
| JP2003513955A5 true JP2003513955A5 (https=) | 2011-04-28 |
| JP4778178B2 JP4778178B2 (ja) | 2011-09-21 |
Family
ID=22583193
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001536512A Expired - Fee Related JP4778178B2 (ja) | 1999-10-27 | 2000-10-25 | 実質的に純粋なビカルタミドの合成における中間体の分割 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US6593492B1 (https=) |
| EP (1) | EP1224167A1 (https=) |
| JP (1) | JP4778178B2 (https=) |
| KR (1) | KR20020067509A (https=) |
| CN (1) | CN1413188A (https=) |
| AU (1) | AU2619501A (https=) |
| BR (1) | BR0015124A (https=) |
| CA (1) | CA2389100A1 (https=) |
| CZ (1) | CZ20021434A3 (https=) |
| HK (1) | HK1048299A1 (https=) |
| HU (1) | HUP0203186A2 (https=) |
| IL (2) | IL149256A0 (https=) |
| MX (1) | MXPA02004225A (https=) |
| NO (1) | NO20021999L (https=) |
| NZ (1) | NZ518552A (https=) |
| PL (1) | PL360059A1 (https=) |
| TW (1) | TWI271397B (https=) |
| WO (1) | WO2001034563A1 (https=) |
| ZA (1) | ZA200203228B (https=) |
Families Citing this family (44)
| 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 |
| US7622503B2 (en) | 2000-08-24 | 2009-11-24 | University Of Tennessee Research Foundation | 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 |
| US7547728B2 (en) | 2001-12-06 | 2009-06-16 | 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 |
| 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 |
| US8445534B2 (en) | 2000-08-24 | 2013-05-21 | University Of Tennessee Research Foundation | Treating androgen decline in aging male (ADAM)-associated conditions with SARMs |
| 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 |
| EP1487458B1 (en) | 2002-02-28 | 2011-11-16 | 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 |
| 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 |
| GEP20074191B (en) | 2002-06-17 | 2007-09-10 | Univ Tennessee Res Foundation | N-bridged selective androgen receptor modulators and methods of use thereof |
| US7741371B2 (en) | 2002-06-17 | 2010-06-22 | University Of Tennessee Research Foundation | Selective androgen receptor modulators and methods of use thereof |
| 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 |
| 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 |
| EP1669347A1 (en) * | 2004-12-10 | 2006-06-14 | Helm AG | Process for the preparation of 3-¬(4-fluorophenyl) sulfonyl|-2-hydroxy-2-methyl propionic acid |
| US20060269596A1 (en) * | 2005-01-12 | 2006-11-30 | Gary Liversidge | Controlled release compositions comprising an acylanilide |
| KR20070114343A (ko) * | 2005-03-29 | 2007-12-03 | 유에스브이 리미티드 | 비칼루타미드의 제조 방법 |
| 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 |
| US10010521B2 (en) | 2006-08-24 | 2018-07-03 | 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 |
| 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 |
| US7968603B2 (en) | 2007-09-11 | 2011-06-28 | University Of Tennessee Research Foundation | Solid forms of selective androgen receptor modulators |
| 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 |
| WO2012042532A1 (en) | 2010-09-29 | 2012-04-05 | Shilpa Medicare Limited | Process for preparing bicalutamide |
| 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) |
| 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) |
| 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) |
| US10258596B2 (en) | 2012-07-13 | 2019-04-16 | Gtx, Inc. | Method of treating HER2-positive breast cancers with selective androgen receptor modulators (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) |
| 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) |
| 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) |
| CN104897818A (zh) * | 2015-06-19 | 2015-09-09 | 重庆医药高等专科学校 | 一种同时测定比卡鲁胺中6种有关物质的uplc方法 |
| CN108069887B (zh) * | 2016-11-17 | 2021-04-20 | 山西振东制药股份有限公司 | 一种(r)-比卡鲁胺中间体的制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58183669A (ja) * | 1982-04-19 | 1983-10-26 | Teikoku Chem Ind Corp Ltd | 光学活性なプロピオン酸誘導体の製造方法 |
| 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 |
| PL308473A1 (en) | 1992-10-21 | 1995-08-07 | Pfizer | Enabntiomeric cis-3-(4,6-dihydoxychroman-3-yl methyl)bezoic acids |
| 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 |
-
2000
- 2000-10-25 CN CN00817760A patent/CN1413188A/zh active Pending
- 2000-10-25 NZ NZ518552A patent/NZ518552A/en unknown
- 2000-10-25 EP EP00989719A patent/EP1224167A1/en not_active Withdrawn
- 2000-10-25 HU HU0203186A patent/HUP0203186A2/hu unknown
- 2000-10-25 CZ CZ20021434A patent/CZ20021434A3/cs unknown
- 2000-10-25 KR KR1020027005357A patent/KR20020067509A/ko not_active Withdrawn
- 2000-10-25 HK HK03100398.5A patent/HK1048299A1/zh unknown
- 2000-10-25 MX MXPA02004225A patent/MXPA02004225A/es not_active Application Discontinuation
- 2000-10-25 CA CA002389100A patent/CA2389100A1/en not_active Abandoned
- 2000-10-25 IL IL14925600A patent/IL149256A0/xx unknown
- 2000-10-25 WO PCT/US2000/041609 patent/WO2001034563A1/en not_active Ceased
- 2000-10-25 PL PL36005900A patent/PL360059A1/xx unknown
- 2000-10-25 AU AU26195/01A patent/AU2619501A/en not_active Abandoned
- 2000-10-25 US US09/695,884 patent/US6593492B1/en not_active Expired - Lifetime
- 2000-10-25 JP JP2001536512A patent/JP4778178B2/ja not_active Expired - Fee Related
- 2000-10-25 BR BR0015124-6A patent/BR0015124A/pt not_active Application Discontinuation
- 2000-10-26 TW TW089122556A patent/TWI271397B/zh not_active IP Right Cessation
-
2002
- 2002-04-22 IL IL149256A patent/IL149256A/en not_active IP Right Cessation
- 2002-04-23 ZA ZA200203228A patent/ZA200203228B/en unknown
- 2002-04-26 NO NO20021999A patent/NO20021999L/no unknown
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