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)
Abstract
En metode for tilberedning av en i alt vesentlig ren enantiomer av et acylanilid slik som Casodex® (bicalutamid) og/eller dens derivater som inkluderer å la en intermediær forbindelse med strukturen i henhold til formel (I) hvor R1 er alkyl eller haloalkyl med opp til 4 karbonatomer; R2 er alkyl med opp til 6 karbonatomer; R3 er en direkte kopling med opp til 6 karbonatomer; R4 er alkyl, alkenyl, hydroksyalkyl eller sykloalkyl hver med opp til 6 karboner; eller R4 er fenyl som bærer en, to eller tre substituenter uavhengig valgt fra hydrogen, halogen, nitro, karboksy, karbamoyl og cyano, og alkyl, alkoksy, alkanoyl, alkyltio, alkylsulfinyl, alkylsulfonyl, perfluoralkyl, perfluoralkyltio, perfluoralkylsulfinyl, perfluoralkylsulfonyl, perfluoralkyl, perfluoralkyltio, perfluoralkylsulfinyl, perfluoralkylsulfonyl, alkoksy- karbonyl og N-alkylkarbamoyl hver med opp til 4 karbonato- mer, og fenyl, fenyltio, fenylsulfinyl og fenylsulfonyl; eller R4 er naftyl; eller R4 er en 5- eller 6-leddet mettet eller umettet heterosyklisk forbindelse som inneholder en, to eller tre heteroatomer valgt fra oksygen, nitrogen og svovel, hvilken heterosyklisk forbindelse kan være en enkelt ring eller være koplet til en benzoring, og hvilken heterosyklisk forbindelse er ikke-substituert eller bærer en eller to halogen, cyano eller amino, eller alkyl, alkoksy, alkyltio, alkylsulfinyl eller alkylsulfonyl hver med opp til 4 karbonatomer, eller oksy eller hydroksy substituenter, eller hvilke som hvis tilstrekkelig mettet, kan bære en eller to okso substituenter; og X1 er oksygen, svovel, sulfinyl (-SO-), sulfonyl (-SO2-), imino (-NH-), eller alkylimino (-NR5-) hvor R5 er alkyl med opp til 6 karbonatomer. Den oppløste intermediate forbindelse av formel (I) er deretter behandlet under betingelser tilstrekkelige til å gi en i alt vesentlig ren enantiomer av et acylanilid slik som Casodex® (bicalutamid) og/eller dets derivater.
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 (no) |
| EP (1) | EP1224167A1 (no) |
| JP (1) | JP4778178B2 (no) |
| KR (1) | KR20020067509A (no) |
| CN (1) | CN1413188A (no) |
| AU (1) | AU2619501A (no) |
| BR (1) | BR0015124A (no) |
| CA (1) | CA2389100A1 (no) |
| CZ (1) | CZ20021434A3 (no) |
| HK (1) | HK1048299A1 (no) |
| HU (1) | HUP0203186A2 (no) |
| IL (2) | IL149256A0 (no) |
| MX (1) | MXPA02004225A (no) |
| NO (1) | NO20021999L (no) |
| NZ (1) | NZ518552A (no) |
| PL (1) | PL360059A1 (no) |
| TW (1) | TWI271397B (no) |
| WO (1) | WO2001034563A1 (no) |
| ZA (1) | ZA200203228B (no) |
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
Also Published As
| Publication number | Publication date |
|---|---|
| WO2001034563A1 (en) | 2001-05-17 |
| PL360059A1 (en) | 2004-09-06 |
| IL149256A (en) | 2011-05-31 |
| HUP0203186A2 (hu) | 2003-01-28 |
| NO20021999D0 (no) | 2002-04-26 |
| CZ20021434A3 (cs) | 2002-11-13 |
| AU2619501A (en) | 2001-06-06 |
| KR20020067509A (ko) | 2002-08-22 |
| ZA200203228B (en) | 2003-07-23 |
| JP2003513955A (ja) | 2003-04-15 |
| CN1413188A (zh) | 2003-04-23 |
| TWI271397B (en) | 2007-01-21 |
| IL149256A0 (en) | 2002-11-10 |
| HK1048299A1 (zh) | 2003-03-28 |
| BR0015124A (pt) | 2002-07-02 |
| JP4778178B2 (ja) | 2011-09-21 |
| MXPA02004225A (es) | 2002-10-17 |
| NZ518552A (en) | 2003-10-31 |
| EP1224167A1 (en) | 2002-07-24 |
| US6593492B1 (en) | 2003-07-15 |
| CA2389100A1 (en) | 2001-05-17 |
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