JP2007529446A5 - - Google Patents
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- Publication number
- JP2007529446A5 JP2007529446A5 JP2007503255A JP2007503255A JP2007529446A5 JP 2007529446 A5 JP2007529446 A5 JP 2007529446A5 JP 2007503255 A JP2007503255 A JP 2007503255A JP 2007503255 A JP2007503255 A JP 2007503255A JP 2007529446 A5 JP2007529446 A5 JP 2007529446A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- amino group
- benzothiazole
- tetrahydro
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 claims 22
- 125000003277 amino group Chemical group 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 5
- 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 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 230000015572 biosynthetic process Effects 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 4
- 239000012445 acidic reagent Substances 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 239000012948 isocyanate Substances 0.000 claims 3
- 150000002513 isocyanates Chemical class 0.000 claims 3
- 230000000269 nucleophilic effect Effects 0.000 claims 3
- FASDKYOPVNHBLU-ZETCQYMHSA-N pramipexole Chemical compound C1[C@@H](NCCC)CCC2=C1SC(N)=N2 FASDKYOPVNHBLU-ZETCQYMHSA-N 0.000 claims 3
- 229960003089 pramipexole Drugs 0.000 claims 3
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 238000010791 quenching Methods 0.000 claims 2
- 230000000171 quenching effect Effects 0.000 claims 2
- 230000008707 rearrangement Effects 0.000 claims 2
- OTLJUTZKDDNQQY-ZCFIWIBFSA-N (6r)-2-acetamido-4,5,6,7-tetrahydro-1,3-benzothiazole-6-carboxylic acid Chemical compound C1C[C@@H](C(O)=O)CC2=C1N=C(NC(=O)C)S2 OTLJUTZKDDNQQY-ZCFIWIBFSA-N 0.000 claims 1
- HMWSDSXKIAJHFQ-LURJTMIESA-N (6s)-2-(propanoylamino)-4,5,6,7-tetrahydro-1,3-benzothiazole-6-carboxylic acid Chemical compound C1C[C@H](C(O)=O)CC2=C1N=C(NC(=O)CC)S2 HMWSDSXKIAJHFQ-LURJTMIESA-N 0.000 claims 1
- OTLJUTZKDDNQQY-LURJTMIESA-N (6s)-2-acetamido-4,5,6,7-tetrahydro-1,3-benzothiazole-6-carboxylic acid Chemical compound C1C[C@H](C(O)=O)CC2=C1N=C(NC(=O)C)S2 OTLJUTZKDDNQQY-LURJTMIESA-N 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- HMWSDSXKIAJHFQ-UHFFFAOYSA-N 2-(propanoylamino)-4,5,6,7-tetrahydro-1,3-benzothiazole-6-carboxylic acid Chemical compound C1CC(C(O)=O)CC2=C1N=C(NC(=O)CC)S2 HMWSDSXKIAJHFQ-UHFFFAOYSA-N 0.000 claims 1
- OTLJUTZKDDNQQY-UHFFFAOYSA-N 2-acetamido-4,5,6,7-tetrahydro-1,3-benzothiazole-6-carboxylic acid Chemical compound C1CC(C(O)=O)CC2=C1N=C(NC(=O)C)S2 OTLJUTZKDDNQQY-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- 238000006969 Curtius rearrangement reaction Methods 0.000 claims 1
- 125000004442 acylamino group Chemical group 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- DOOXJKFCYMFGOD-UHFFFAOYSA-N ethyl 2-(propanoylamino)-4,5,6,7-tetrahydro-1,3-benzothiazole-6-carboxylate Chemical compound C1C(C(=O)OCC)CCC2=C1SC(NC(=O)CC)=N2 DOOXJKFCYMFGOD-UHFFFAOYSA-N 0.000 claims 1
- GXJCNUJEVKUQDE-UHFFFAOYSA-N ethyl 2-acetamido-4,5,6,7-tetrahydro-1,3-benzothiazole-6-carboxylate Chemical compound C1C(C(=O)OCC)CCC2=C1SC(NC(C)=O)=N2 GXJCNUJEVKUQDE-UHFFFAOYSA-N 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- XZNCYDMHLCOBDH-UHFFFAOYSA-N methyl 2-(propanoylamino)-4,5,6,7-tetrahydro-1,3-benzothiazole-6-carboxylate Chemical compound C1CC(C(=O)OC)CC2=C1N=C(NC(=O)CC)S2 XZNCYDMHLCOBDH-UHFFFAOYSA-N 0.000 claims 1
- QAKBICNXVCOPRS-UHFFFAOYSA-N methyl 2-acetamido-4,5,6,7-tetrahydro-1,3-benzothiazole-6-carboxylate Chemical compound C1C(C(=O)OC)CCC2=C1SC(NC(C)=O)=N2 QAKBICNXVCOPRS-UHFFFAOYSA-N 0.000 claims 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 claims 1
- ZUQZGPGQZDIZLK-UHFFFAOYSA-N propyl 2-(propanoylamino)-4,5,6,7-tetrahydro-1,3-benzothiazole-6-carboxylate Chemical compound C1C(C(=O)OCCC)CCC2=C1SC(NC(=O)CC)=N2 ZUQZGPGQZDIZLK-UHFFFAOYSA-N 0.000 claims 1
- BRLIGTUBZDEGLL-UHFFFAOYSA-N propyl 2-acetamido-4,5,6,7-tetrahydro-1,3-benzothiazole-6-carboxylate Chemical compound C1C(C(=O)OCCC)CCC2=C1SC(NC(C)=O)=N2 BRLIGTUBZDEGLL-UHFFFAOYSA-N 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 238000006462 rearrangement reaction Methods 0.000 claims 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims 1
- -1 silylamino group Chemical group 0.000 claims 1
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 1
- 239000012279 sodium borohydride Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI20040531 ITMI20040531A1 (it) | 2004-03-19 | 2004-03-19 | Intermedi per la preparazione di pramipexolo |
| ITMI20050126 ITMI20050126A1 (it) | 2005-01-28 | 2005-01-28 | Intermedi per la preparazione di pramipexolo |
| PCT/EP2005/002641 WO2005092871A2 (en) | 2004-03-19 | 2005-03-11 | Intermediates for the preparation of pramipexole |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007529446A JP2007529446A (ja) | 2007-10-25 |
| JP2007529446A5 true JP2007529446A5 (enExample) | 2008-03-27 |
Family
ID=34963371
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007503255A Pending JP2007529446A (ja) | 2004-03-19 | 2005-03-11 | プラミペキソールの製造のための中間体 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US7741490B2 (enExample) |
| EP (2) | EP2289885A1 (enExample) |
| JP (1) | JP2007529446A (enExample) |
| AT (1) | ATE496036T1 (enExample) |
| CA (1) | CA2560128A1 (enExample) |
| DE (1) | DE602005025988D1 (enExample) |
| IL (1) | IL178156A0 (enExample) |
| WO (1) | WO2005092871A2 (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL378587A1 (pl) * | 2005-12-29 | 2007-07-09 | Instytut Farmaceutyczny | Sposób wytwarzania (S)-(-)-2-amino-6-n-propyloamino-4,5,6,7-tetrahydrobenzotiazolu i/lub jego soli |
| ITMI20060044A1 (it) | 2006-01-13 | 2007-07-14 | Dipharma Spa | Sintesi di intermedi pr la preparazione di pramipexolo |
| US8518926B2 (en) * | 2006-04-10 | 2013-08-27 | Knopp Neurosciences, Inc. | Compositions and methods of using (R)-pramipexole |
| ES2379117T3 (es) | 2006-05-16 | 2012-04-20 | Knopp Neurosciences, Inc. | Composiciones de R(+) y S(-) pramipexol y métodos de utilización de las mismas |
| EP1878731B1 (en) * | 2006-06-26 | 2008-08-20 | Helm AG | Process for producing pramipexole |
| US8524695B2 (en) | 2006-12-14 | 2013-09-03 | Knopp Neurosciences, Inc. | Modified release formulations of (6R)-4,5,6,7-tetrahydro-N6-propyl-2,6-benzothiazole-diamine and methods of using the same |
| WO2008113056A2 (en) | 2007-03-14 | 2008-09-18 | Knopp Neurosciences, Inc. | Synthesis of chirally purified substituted benzothiazole diamines |
| GB0721332D0 (en) * | 2007-10-31 | 2007-12-12 | Motac Neuroscience Ltd | Medicaments |
| GB0721333D0 (en) * | 2007-10-31 | 2007-12-12 | Motac Neuroscience Ltd | Medicaments |
| CN102186350A (zh) * | 2008-08-19 | 2011-09-14 | 诺普神经科学股份有限公司 | 使用(r)-普拉克索的组合物与方法 |
| CN101676272A (zh) * | 2008-09-17 | 2010-03-24 | 北京德众万全药物技术开发有限公司 | 一种普拉克索的制备方法 |
| WO2011021214A2 (en) * | 2009-08-07 | 2011-02-24 | Msn Laboratories Limited | Improved process for the preparation of (s)-2-amino-4,5,6,7-tetrahydro-6 - (propylamino) benzothiazole and its pharmaceutically acceptable salts |
| ITMI20101998A1 (it) * | 2010-10-27 | 2012-04-28 | Dipharma Francis Srl | Procedimento per la racemizzazione di acidi carbossilici |
| CN102442972B (zh) * | 2011-10-18 | 2014-06-25 | 济南富创医药科技有限公司 | 一种普拉克索及其二盐酸盐一水合物的工业化制备方法 |
| WO2013096816A1 (en) | 2011-12-22 | 2013-06-27 | Biogen Idec Ma Inc. | Improved synthesis of amine substituted 4,5,6,7-tetrahydrobenzothiazole compounds |
| CN103183650A (zh) * | 2011-12-31 | 2013-07-03 | 天津药物研究院 | (s)-(-)2-氨基-6-丙氨基-4,5,6,7-四氢苯并噻唑的制备方法 |
| CN103183649A (zh) * | 2011-12-31 | 2013-07-03 | 天津药物研究院 | 2-氨基-6-丙氨基-4,5,6,7-四氢苯并噻唑的制备方法 |
| US9662313B2 (en) | 2013-02-28 | 2017-05-30 | Knopp Biosciences Llc | Compositions and methods for treating amyotrophic lateral sclerosis in responders |
| US9468630B2 (en) | 2013-07-12 | 2016-10-18 | Knopp Biosciences Llc | Compositions and methods for treating conditions related to increased eosinophils |
| SMT202100119T1 (it) | 2013-07-12 | 2021-05-07 | Knopp Biosciences Llc | Trattamento dei livelli elevati di eosinofili e/o basofili |
| EP3038467B1 (en) | 2013-08-13 | 2020-07-29 | Knopp Biosciences LLC | Compositions and methods for treating plasma cell disorders and b-cell prolymphocytic disorders |
| AU2014306597B2 (en) | 2013-08-13 | 2018-05-17 | Knopp Biosciences Llc | Compositions and methods for treating chronic urticaria |
| KR20230067604A (ko) * | 2020-08-05 | 2023-05-16 | 아레테이아 테라퓨틱스, 인코포레이티드 | 중등도 내지 중증 천식의 치료를 위한 덱스프라미펙솔의 용도 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3447075A1 (de) * | 1984-12-22 | 1986-07-03 | Dr. Karl Thomae Gmbh, 7950 Biberach | Tetrahydro-benzthiazole, deren herstellung und deren verwendung als zwischenprodukte oder als arzneimittel |
| ATE45735T1 (de) | 1984-12-22 | 1989-09-15 | Thomae Gmbh Dr K | Tetrahydro-benzthiazole, deren herstellung und deren verwendung als zwischenprodukte oder als arnzneimittel. |
| ZA864626B (en) | 1985-06-24 | 1988-02-24 | Lilly Co Eli | Dialkylaminotetrahydrobenzothiazoles and oxazoles |
| US4988699A (en) * | 1989-03-14 | 1991-01-29 | Warner-Lambert Company | Substituted tetrahydrobenzothiazoles as dopaminergic agents |
| PL341356A1 (en) * | 1997-12-22 | 2001-04-09 | Bayer Ag | Raf kinase inhibition employing aryl- and heteroaryl-substituted heterocyclic ureas |
| JP2000119226A (ja) * | 1998-10-13 | 2000-04-25 | Banyu Pharmaceut Co Ltd | クルチウス転移反応を固相合成に利用した新規な芳香族アミン類又は芳香族複素環アミン類の製造方法 |
| ES2187249B1 (es) | 2000-09-18 | 2004-09-16 | Synthon Bv | Procedimiento para la preparacion de 2-amino-6-(alquil)amino-4,5,6,7-tetrahidrobenzotiazoles. |
| JP2002173476A (ja) * | 2000-12-07 | 2002-06-21 | Sumitomo Pharmaceut Co Ltd | １，４−フェニレンジアミン誘導体及びその製造法 |
| CL2004000553A1 (es) * | 2003-03-20 | 2005-02-04 | Actelion Pharmaceuticals Ltd | Uso de compuestos derivados de guanidina como antagonistas del receptor de neuropeptido ff; compuestos derivados de guanidina; procedimientos de preparacion; y composicion farmaceutica que los comprende. |
| EP1640369A4 (en) * | 2003-06-27 | 2007-10-31 | Dainippon Sumitomo Pharma Co | THIAZOLIMINE COMPOUND AND OXAZOLIMINE COMPOUND |
-
2005
- 2005-03-11 EP EP10180254A patent/EP2289885A1/en not_active Withdrawn
- 2005-03-11 EP EP05728706A patent/EP1730129B1/en not_active Expired - Lifetime
- 2005-03-11 CA CA002560128A patent/CA2560128A1/en not_active Abandoned
- 2005-03-11 WO PCT/EP2005/002641 patent/WO2005092871A2/en not_active Ceased
- 2005-03-11 JP JP2007503255A patent/JP2007529446A/ja active Pending
- 2005-03-11 AT AT05728706T patent/ATE496036T1/de not_active IP Right Cessation
- 2005-03-11 DE DE602005025988T patent/DE602005025988D1/de not_active Expired - Lifetime
- 2005-03-11 US US10/593,269 patent/US7741490B2/en not_active Expired - Fee Related
-
2006
- 2006-09-18 IL IL178156A patent/IL178156A0/en unknown
-
2010
- 2010-05-10 US US12/776,588 patent/US8203002B2/en not_active Expired - Fee Related
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