JP2003513955A5 - - Google Patents
Download PDFInfo
- 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 |
| 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 |
| US8445534B2 (en) | 2000-08-24 | 2013-05-21 | University Of Tennessee Research Foundation | Treating androgen decline in aging male (ADAM)-associated conditions with SARMs |
| 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 |
| 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 |
| 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 |
| US7741371B2 (en) | 2002-06-17 | 2010-06-22 | University Of Tennessee Research Foundation | Selective androgen receptor modulators and methods of use thereof |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| ES2581765T3 (es) | 2006-08-24 | 2016-09-07 | University Of Tennessee Research Foundation | Acilanilidas sustituidas y métodos de uso de las mismas |
| 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 |
| 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 |
| LT2872482T (lt) | 2012-07-13 | 2020-12-28 | Oncternal Therapeutics, Inc. | Krūties vėžių gydymo būdas selektyviu androgeno receptoriaus moduliatoriumi |
| 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) |
| 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) |
| 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) |
| 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) |
| US10314807B2 (en) | 2012-07-13 | 2019-06-11 | Gtx, Inc. | Method of treating HER2-positive 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 |
| ATE28864T1 (de) * | 1982-07-23 | 1987-08-15 | Ici Plc | Amide-derivate. |
| 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 |
| 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 |
-
2000
- 2000-10-25 CN CN00817760A patent/CN1413188A/zh active Pending
- 2000-10-25 CZ CZ20021434A patent/CZ20021434A3/cs unknown
- 2000-10-25 BR BR0015124-6A patent/BR0015124A/pt not_active Application Discontinuation
- 2000-10-25 NZ NZ518552A patent/NZ518552A/en unknown
- 2000-10-25 EP EP00989719A patent/EP1224167A1/en not_active Withdrawn
- 2000-10-25 WO PCT/US2000/041609 patent/WO2001034563A1/en not_active Ceased
- 2000-10-25 MX MXPA02004225A patent/MXPA02004225A/es not_active Application Discontinuation
- 2000-10-25 JP JP2001536512A patent/JP4778178B2/ja not_active Expired - Fee Related
- 2000-10-25 KR KR1020027005357A patent/KR20020067509A/ko not_active Withdrawn
- 2000-10-25 IL IL14925600A patent/IL149256A0/xx unknown
- 2000-10-25 US US09/695,884 patent/US6593492B1/en not_active Expired - Lifetime
- 2000-10-25 HK HK03100398.5A patent/HK1048299A1/zh unknown
- 2000-10-25 PL PL36005900A patent/PL360059A1/xx unknown
- 2000-10-25 AU AU26195/01A patent/AU2619501A/en not_active Abandoned
- 2000-10-25 HU HU0203186A patent/HUP0203186A2/hu unknown
- 2000-10-25 CA CA002389100A patent/CA2389100A1/en not_active Abandoned
- 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
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2003513955A5 (https=) | ||
| JP4778178B2 (ja) | 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 | |
| JP4358518B2 (ja) | ビカルタミドを含むアシルアニリドおよびそれらの誘導体を合成する方法 | |
| KR100207145B1 (ko) | (-)-((4-(1,4,5,6-테트라하이드로-4-메틸-6-옥소-3-피리다지닐)페닐히드라조노)프로판디니트릴 | |
| JP2008523069A5 (https=) | ||
| HUP0203785A2 (hu) | Eljárás Casodex enantiomereinek, származékainak és intermediereinek előállítására | |
| EP3094632A1 (en) | 5-fluoro-4-imino-3-(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1h)-one and processes for their preparation | |
| CN102558150A (zh) | 取代亚砜化合物的合成方法 | |
| KR20100020035A (ko) | 생활성 화합물의 설폭사이드화 방법 | |
| CN103833731B (zh) | 手性亚砜类化合物及其盐的制备新方法和晶型 | |
| RU2676332C1 (ru) | Способ получения 3-замещённых сложных эфиров (индол-1-ил)-уксусной кислоты | |
| JP2008501740A (ja) | ２−オキソ−１−ピロリジン誘導体の製造方法 | |
| JP2013540780A (ja) | イミダゾール誘導体並びにその製造法及び使用 | |
| JP2005530795A (ja) | ビカルタミドの製造方法 | |
| JP2005514422A5 (https=) | ||
| CN115093360B (zh) | 一种吲哚类衍生物的合成方法 | |
| BG103259A (bg) | Стереоспецифично получаване на хирални 1-арил- и 1- хетероарил-заместени етил-2-амини | |
| CN101341144A (zh) | 对映选择性制备苯并咪唑衍生物和其盐 | |
| RU2002113660A (ru) | Разделение промежуточных соединений при синтезе практически чистого бикалутамида | |
| CN1789265A (zh) | 新颖的取代的1H－吡咯并[2，3－b]吡啶及其制备方法 | |
| RU2574734C1 (ru) | Способ получения оптически чистых хиральных пиридилсульфинильных производных бензимидазолов | |
| EP2888250A1 (en) | Process for the synthesis of substituted gamma lactams | |
| JP5943387B2 (ja) | 新規トリフロン誘導体及びその製造方法 | |
| TW202346260A (zh) | 用於製備5-氯-2-((乙氧基羰基)胺基)-3-甲基苯甲酸之方法 | |
| JP3564791B2 (ja) | α−アミノケトン類の製造方法 |