NO20021999L - Spaltning av intermediater i syntesen av hovedsakelig rent bicalutamid - Google Patents
Spaltning av intermediater i syntesen av hovedsakelig rent bicalutamidInfo
- Publication number
- NO20021999L NO20021999L NO20021999A NO20021999A NO20021999L NO 20021999 L NO20021999 L NO 20021999L NO 20021999 A NO20021999 A NO 20021999A NO 20021999 A NO20021999 A NO 20021999A NO 20021999 L NO20021999 L NO 20021999L
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- carbon atoms
- perfluoroalkylsulfinyl
- substantially pure
- bicalutamide
- Prior art date
Links
- 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 title abstract 3
- 229960000997 bicalutamide Drugs 0.000 title abstract 3
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003776 cleavage reaction Methods 0.000 title 1
- 239000000543 intermediate Substances 0.000 title 1
- 230000007017 scission Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- 125000004432 carbon atom Chemical group C* 0.000 abstract 6
- -1 acyl anilide Chemical class 0.000 abstract 4
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 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 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 abstract 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 2
- 125000004414 alkyl thio group Chemical group 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 229940097647 casodex Drugs 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 229920006395 saturated elastomer Polymers 0.000 abstract 2
- 229910052717 sulfur Chemical group 0.000 abstract 2
- 239000011593 sulfur Chemical group 0.000 abstract 2
- 125000005118 N-alkylcarbamoyl group Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000005277 alkyl imino group Chemical group 0.000 abstract 1
- 125000005605 benzo group Chemical group 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 230000008878 coupling Effects 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 125000001841 imino group Chemical group [H]N=* 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 abstract 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 abstract 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=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
- C07C315/06—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/26—Separation; Purification; Stabilisation; Use of additives
- C07C319/28—Separation; Purification
-
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16188499P | 1999-10-27 | 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 (2)
| Publication Number | Publication Date |
|---|---|
| NO20021999D0 NO20021999D0 (no) | 2002-04-26 |
| NO20021999L true NO20021999L (no) | 2002-06-20 |
Family
ID=22583193
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20021999A NO20021999L (no) | 1999-10-27 | 2002-04-26 | Spaltning av intermediater i syntesen av hovedsakelig rent bicalutamid |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US6593492B1 (cs) |
| EP (1) | EP1224167A1 (cs) |
| JP (1) | JP4778178B2 (cs) |
| KR (1) | KR20020067509A (cs) |
| CN (1) | CN1413188A (cs) |
| AU (1) | AU2619501A (cs) |
| BR (1) | BR0015124A (cs) |
| CA (1) | CA2389100A1 (cs) |
| CZ (1) | CZ20021434A3 (cs) |
| HK (1) | HK1048299A1 (cs) |
| HU (1) | HUP0203186A2 (cs) |
| IL (2) | IL149256A0 (cs) |
| MX (1) | MXPA02004225A (cs) |
| NO (1) | NO20021999L (cs) |
| NZ (1) | NZ518552A (cs) |
| PL (1) | PL360059A1 (cs) |
| TW (1) | TWI271397B (cs) |
| WO (1) | WO2001034563A1 (cs) |
| ZA (1) | ZA200203228B (cs) |
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 |
| 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 |
| 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 |
| CA2448571A1 (en) * | 2001-06-13 | 2002-12-19 | Biogal Gyogyszergyar Rt. | Novel process for preparing rac-bicalutamide and its intermediates |
| BR0215115A (pt) | 2001-12-06 | 2005-04-19 | Gtx Inc | Tratamento de perda muscular com moduladores de receptores de androgênio seletivos |
| US8853266B2 (en) | 2001-12-06 | 2014-10-07 | University Of Tennessee Research Foundation | Selective androgen receptor modulators for treating diabetes |
| DE60233526D1 (de) | 2001-12-13 | 2009-10-08 | Sumitomo Chemical Co | Bicalutamidkristalle und verfahren zu deren herstellung |
| CA2689080C (en) | 2002-02-07 | 2011-07-05 | University Of Tennessee Research Foundation | Treating benign prostate hyperplasia with sarms |
| WO2003074450A2 (en) | 2002-02-28 | 2003-09-12 | The University Of Tennessee Research Corporation | Radiolabeled selective androgen receptor modulators and their use in prostate cancer imaging and therapy |
| US7772433B2 (en) | 2002-02-28 | 2010-08-10 | University Of Tennessee Research Foundation | SARMS and method of use thereof |
| EP1487458B1 (en) | 2002-02-28 | 2011-11-16 | University Of Tennessee Research Foundation | Multi-substituted selective androgen receptor modulators and methods 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 |
| US7741371B2 (en) | 2002-06-17 | 2010-06-22 | University Of Tennessee Research Foundation | Selective androgen receptor modulators and methods of use thereof |
| BR0312172A (pt) | 2002-06-17 | 2005-04-05 | Univ Tennessee Res Foundation | Moduladores seletivos receptores de androgênio em ponte de nitrogênio e seus métodos de uso |
| 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 |
| WO2006103689A1 (en) * | 2005-03-29 | 2006-10-05 | Usv Limited | Process for preparation of bicalutamide |
| 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 |
| US10010521B2 (en) | 2006-08-24 | 2018-07-03 | 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 |
| PT2054049E (pt) | 2006-08-24 | 2016-06-02 | Univ Tennessee Res Found | Acilanilidas substituídas e métodos de utilização das mesmas |
| US7968603B2 (en) | 2007-09-11 | 2011-06-28 | University Of Tennessee Research Foundation | Solid forms of selective androgen receptor modulators |
| 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 |
| 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 |
| 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) |
| 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) |
| 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) |
| RU2648959C2 (ru) | 2012-07-13 | 2018-03-28 | Джи Ти Икс, ИНК. | Способ лечения андроген-рецептора(ar)-положительных форм рака молочной железы с использованием селективных модуляторов андрогенных рецепторов(sarm) |
| US10258596B2 (en) | 2012-07-13 | 2019-04-16 | Gtx, Inc. | Method of treating HER2-positive breast cancers with selective androgen receptor modulators (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) |
| 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 |
| 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 |
| WO1994008986A1 (en) | 1992-10-21 | 1994-04-28 | Pfizer, Inc. | Enantiomeric cis-3-(4,6-dihydroxychroman-3-yl-methyl)benzoic 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 |
| 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 |
-
2000
- 2000-10-25 PL PL36005900A patent/PL360059A1/xx unknown
- 2000-10-25 CA CA002389100A patent/CA2389100A1/en not_active Abandoned
- 2000-10-25 MX MXPA02004225A patent/MXPA02004225A/es not_active Application Discontinuation
- 2000-10-25 BR BR0015124-6A patent/BR0015124A/pt not_active Application Discontinuation
- 2000-10-25 EP EP00989719A patent/EP1224167A1/en not_active Withdrawn
- 2000-10-25 HK HK03100398.5A patent/HK1048299A1/zh unknown
- 2000-10-25 IL IL14925600A patent/IL149256A0/xx unknown
- 2000-10-25 AU AU26195/01A patent/AU2619501A/en not_active Abandoned
- 2000-10-25 KR KR1020027005357A patent/KR20020067509A/ko not_active Withdrawn
- 2000-10-25 CN CN00817760A patent/CN1413188A/zh active Pending
- 2000-10-25 WO PCT/US2000/041609 patent/WO2001034563A1/en not_active Application Discontinuation
- 2000-10-25 HU HU0203186A patent/HUP0203186A2/hu unknown
- 2000-10-25 JP JP2001536512A patent/JP4778178B2/ja not_active Expired - Fee Related
- 2000-10-25 US US09/695,884 patent/US6593492B1/en not_active Expired - Lifetime
- 2000-10-25 NZ NZ518552A patent/NZ518552A/en unknown
- 2000-10-25 CZ CZ20021434A patent/CZ20021434A3/cs unknown
- 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
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA02004225A (es) | 2002-10-17 |
| AU2619501A (en) | 2001-06-06 |
| CN1413188A (zh) | 2003-04-23 |
| JP2003513955A (ja) | 2003-04-15 |
| ZA200203228B (en) | 2003-07-23 |
| HUP0203186A2 (hu) | 2003-01-28 |
| WO2001034563A1 (en) | 2001-05-17 |
| CA2389100A1 (en) | 2001-05-17 |
| TWI271397B (en) | 2007-01-21 |
| BR0015124A (pt) | 2002-07-02 |
| EP1224167A1 (en) | 2002-07-24 |
| NO20021999D0 (no) | 2002-04-26 |
| HK1048299A1 (zh) | 2003-03-28 |
| CZ20021434A3 (cs) | 2002-11-13 |
| JP4778178B2 (ja) | 2011-09-21 |
| NZ518552A (en) | 2003-10-31 |
| IL149256A0 (en) | 2002-11-10 |
| IL149256A (en) | 2011-05-31 |
| PL360059A1 (en) | 2004-09-06 |
| US6593492B1 (en) | 2003-07-15 |
| KR20020067509A (ko) | 2002-08-22 |
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