ZA200503548B - Process for preparing 2,6-diamond-4,5,6,7-Tetrahydro-Benzothiazole - Google Patents
Process for preparing 2,6-diamond-4,5,6,7-Tetrahydro-Benzothiazole Download PDFInfo
- Publication number
- ZA200503548B ZA200503548B ZA200503548A ZA200503548A ZA200503548B ZA 200503548 B ZA200503548 B ZA 200503548B ZA 200503548 A ZA200503548 A ZA 200503548A ZA 200503548 A ZA200503548 A ZA 200503548A ZA 200503548 B ZA200503548 B ZA 200503548B
- Authority
- ZA
- South Africa
- Prior art keywords
- tetrahydro
- diamino
- acetamido
- steps
- benzothiazole
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 238000000034 method Methods 0.000 claims description 28
- DRRYZHHKWSHHFT-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1,3-benzothiazole-2,6-diamine Chemical compound C1C(N)CCC2=C1SC(N)=N2 DRRYZHHKWSHHFT-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 18
- FASDKYOPVNHBLU-ZETCQYMHSA-N pramipexole Chemical compound C1[C@@H](NCCC)CCC2=C1SC(N)=N2 FASDKYOPVNHBLU-ZETCQYMHSA-N 0.000 claims description 17
- 229960003089 pramipexole Drugs 0.000 claims description 15
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- WZEMYWNHKFIVKE-UHFFFAOYSA-N n-(4-oxocyclohexyl)acetamide Chemical compound CC(=O)NC1CCC(=O)CC1 WZEMYWNHKFIVKE-UHFFFAOYSA-N 0.000 claims description 11
- 239000000243 solution Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 238000002955 isolation Methods 0.000 claims description 9
- HWAFCRWGGRVEQL-UHFFFAOYSA-N n-(4-hydroxycyclohexyl)acetamide Chemical compound CC(=O)NC1CCC(O)CC1 HWAFCRWGGRVEQL-UHFFFAOYSA-N 0.000 claims description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 6
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 3
- 230000031709 bromination Effects 0.000 claims description 3
- 238000005893 bromination reaction Methods 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 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 description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- -1 propionyl halide Chemical class 0.000 claims description 2
- QXKCTWPNUINDQK-UHFFFAOYSA-N n-(2-amino-4,5,6,7-tetrahydro-1,3-benzothiazol-6-yl)acetamide Chemical compound C1C(NC(=O)C)CCC2=C1SC(N)=N2 QXKCTWPNUINDQK-UHFFFAOYSA-N 0.000 claims 2
- 238000010992 reflux Methods 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000003810 Jones reagent Substances 0.000 description 2
- 239000005708 Sodium hypochlorite Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- UJAXXUXPLJRDOH-UHFFFAOYSA-N 2-bromo-4-tert-butylcyclohexan-1-one Chemical class CC(C)(C)C1CCC(=O)C(Br)C1 UJAXXUXPLJRDOH-UHFFFAOYSA-N 0.000 description 1
- KDXYEWRAWRZXFT-UHFFFAOYSA-N 2-bromocyclohexan-1-one Chemical compound BrC1CCCCC1=O KDXYEWRAWRZXFT-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 239000001358 L(+)-tartaric acid Substances 0.000 description 1
- 235000011002 L(+)-tartaric acid Nutrition 0.000 description 1
- FEWJPZIEWOKRBE-LWMBPPNESA-N L-(+)-Tartaric acid Natural products OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- JHIVVAPYMSGYDF-PTQBSOBMSA-N cyclohexanone Chemical class O=[13C]1CCCCC1 JHIVVAPYMSGYDF-PTQBSOBMSA-N 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- MSMGDVQGSDAMKR-UHFFFAOYSA-N n-(2-amino-4,5,6,7-tetrahydro-1,3-benzothiazol-6-yl)acetamide;dihydrobromide Chemical compound Br.Br.C1C(NC(=O)C)CCC2=C1SC(N)=N2 MSMGDVQGSDAMKR-UHFFFAOYSA-N 0.000 description 1
- WBTGJPGTKKCSKY-UHFFFAOYSA-N n-(3-bromo-4-oxocyclohexyl)acetamide Chemical compound CC(=O)NC1CCC(=O)C(Br)C1 WBTGJPGTKKCSKY-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- RIBFXMJCUYXJDZ-UHFFFAOYSA-N propanoyl bromide Chemical compound CCC(Br)=O RIBFXMJCUYXJDZ-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000006207 propylation Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/82—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0225701A GB2394951A (en) | 2002-11-04 | 2002-11-04 | One pot synthesis of 2,6-diamino-4,5,6,7-tetrahydro-benzothiazole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200503548B true ZA200503548B (en) | 2006-12-27 |
Family
ID=9947186
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200503548A ZA200503548B (en) | 2002-11-04 | 2003-11-03 | Process for preparing 2,6-diamond-4,5,6,7-Tetrahydro-Benzothiazole |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US7285669B2 (pl) |
| EP (1) | EP1562921B1 (pl) |
| JP (1) | JP4708792B2 (pl) |
| KR (1) | KR101086844B1 (pl) |
| CN (1) | CN100551918C (pl) |
| AP (1) | AP1882A (pl) |
| AT (1) | ATE396180T1 (pl) |
| AU (1) | AU2003278396B2 (pl) |
| BR (1) | BR0315919A (pl) |
| CA (1) | CA2505179C (pl) |
| DE (1) | DE60321208D1 (pl) |
| EC (1) | ECSP055835A (pl) |
| GB (1) | GB2394951A (pl) |
| HR (1) | HRPK20050403B3 (pl) |
| IS (1) | IS7882A (pl) |
| MA (1) | MA27534A1 (pl) |
| MX (1) | MXPA05004815A (pl) |
| NO (1) | NO20052189L (pl) |
| NZ (1) | NZ539953A (pl) |
| PL (1) | PL376543A1 (pl) |
| PT (1) | PT1562921E (pl) |
| RU (1) | RU2305097C2 (pl) |
| TN (1) | TNSN05125A1 (pl) |
| WO (1) | WO2004041797A1 (pl) |
| ZA (1) | ZA200503548B (pl) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0221513D0 (en) * | 2002-09-17 | 2002-10-23 | Generics Uk Ltd | Novel compounds and processes |
| WO2006012277A2 (en) * | 2004-06-30 | 2006-02-02 | Amr Technology, Inc. | Biocatalytic process for preparing enantiomerically enriched pramipexole |
| WO2006003677A1 (en) * | 2004-07-01 | 2006-01-12 | Alembic Limited | Improved process for the preparation of biologically active tetrahydrobenzthiazole derivative |
| 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 |
| 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 |
| SI22446A (sl) * | 2007-02-07 | 2008-08-31 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Nov postopek za sintezo pramipeksola in njegovih farmacevtsko sprejemljivih soli |
| WO2008104847A2 (en) * | 2007-02-26 | 2008-09-04 | Wockhardt Research Centre | Processes for the preparation of pramipexole and salts thereof |
| JP2010521496A (ja) * | 2007-03-14 | 2010-06-24 | ノップ ニューロサイエンシーズ、インク． | キラル精製置換ベンゾチアゾールジアミンの合成 |
| CN101429173B (zh) * | 2007-11-09 | 2012-12-05 | 重庆医药工业研究院有限责任公司 | 一种普拉克索中间体2,6-二氨基-4,5,6,7-四氢-苯并噻唑的制备方法 |
| US20110190356A1 (en) | 2008-08-19 | 2011-08-04 | Knopp Neurosciences Inc. | Compositions and Methods of Using (R)- Pramipexole |
| 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 |
| WO2013096816A1 (en) | 2011-12-22 | 2013-06-27 | Biogen Idec Ma Inc. | Improved synthesis of amine substituted 4,5,6,7-tetrahydrobenzothiazole compounds |
| 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 |
| LT3019167T (lt) | 2013-07-12 | 2021-03-25 | Knopp Biosciences Llc | Eozinofilų ir (arba) bazofilų padidintų kiekių gydymas |
| AU2014306597B2 (en) | 2013-08-13 | 2018-05-17 | Knopp Biosciences Llc | Compositions and methods for treating chronic urticaria |
| EP3038467B1 (en) | 2013-08-13 | 2020-07-29 | Knopp Biosciences LLC | Compositions and methods for treating plasma cell disorders and b-cell prolymphocytic disorders |
| CN104311507A (zh) * | 2013-10-09 | 2015-01-28 | 安徽万邦医药科技有限公司 | (6s)-2,6-二氨基-4,5,6,7-四氢苯并噻唑的制备方法 |
| CN103613562B (zh) * | 2013-11-25 | 2015-09-30 | 浙江美诺华药物化学有限公司 | 一种普拉克索的制备方法 |
| CN107573301B (zh) * | 2017-11-08 | 2020-08-11 | 江苏长青农化股份有限公司 | 一种三环唑中间体的制备方法 |
| CN109232471B (zh) * | 2018-10-31 | 2022-05-10 | 安徽省庆云医药股份有限公司 | 一种盐酸普拉克索的制备方法 |
| CN111362884A (zh) * | 2018-12-26 | 2020-07-03 | 江苏神龙药业股份有限公司 | 一种2,6-二氨基-4,5,6,7-四氢-苯并噻唑的工业化制备方法 |
| CN110734413A (zh) * | 2019-12-02 | 2020-01-31 | 山东铂源药业有限公司 | 一种普拉克索中间体2,6-二氨基-4,5,6,7-四氢苯并噻唑的制备方法 |
Family Cites Families (3)
| 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 |
| EP0186087B1 (de) * | 1984-12-22 | 1989-08-23 | Dr. Karl Thomae GmbH | Tetrahydro-benzthiazole, deren Herstellung und deren Verwendung als Zwischenprodukte oder als Arnzneimittel |
| 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. |
-
2002
- 2002-11-04 GB GB0225701A patent/GB2394951A/en not_active Withdrawn
-
2003
- 2003-11-03 CN CNB2003801082013A patent/CN100551918C/zh not_active Expired - Fee Related
- 2003-11-03 JP JP2004549326A patent/JP4708792B2/ja not_active Expired - Fee Related
- 2003-11-03 ZA ZA200503548A patent/ZA200503548B/en unknown
- 2003-11-03 AP AP2005003306A patent/AP1882A/xx active
- 2003-11-03 CA CA2505179A patent/CA2505179C/en not_active Expired - Fee Related
- 2003-11-03 AU AU2003278396A patent/AU2003278396B2/en not_active Ceased
- 2003-11-03 AT AT03769701T patent/ATE396180T1/de not_active IP Right Cessation
- 2003-11-03 MX MXPA05004815A patent/MXPA05004815A/es active IP Right Grant
- 2003-11-03 PL PL376543A patent/PL376543A1/pl not_active IP Right Cessation
- 2003-11-03 PT PT03769701T patent/PT1562921E/pt unknown
- 2003-11-03 BR BR0315919-1A patent/BR0315919A/pt not_active IP Right Cessation
- 2003-11-03 EP EP03769701A patent/EP1562921B1/en not_active Expired - Lifetime
- 2003-11-03 KR KR1020057007963A patent/KR101086844B1/ko not_active IP Right Cessation
- 2003-11-03 WO PCT/GB2003/004734 patent/WO2004041797A1/en active IP Right Grant
- 2003-11-03 US US10/533,637 patent/US7285669B2/en not_active Expired - Fee Related
- 2003-11-03 NZ NZ539953A patent/NZ539953A/en not_active IP Right Cessation
- 2003-11-03 DE DE60321208T patent/DE60321208D1/de not_active Expired - Lifetime
- 2003-11-03 RU RU2005117364/04A patent/RU2305097C2/ru not_active IP Right Cessation
-
2005
- 2005-05-04 NO NO20052189A patent/NO20052189L/no unknown
- 2005-05-04 TN TNP2005000125A patent/TNSN05125A1/en unknown
- 2005-05-05 HR HR20050403A patent/HRPK20050403B3/xx not_active IP Right Cessation
- 2005-06-02 IS IS7882A patent/IS7882A/is unknown
- 2005-06-02 MA MA28311A patent/MA27534A1/fr unknown
- 2005-06-03 EC EC2005005835A patent/ECSP055835A/es unknown
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