PE20071148A1 - IMPROVEMENTS IN THE PREPARATION OF INTERMEDIATES LEADING TO HYDROCHLORIDE OF [4- (5-AMINomethyl-2-FLUORO-PHENYL) -PIPERIDIN-1-IL] - (4-BROMO-3-METHYL-5-PROPOXY-THIOFEN-2- IL) -METANONE - Google Patents
IMPROVEMENTS IN THE PREPARATION OF INTERMEDIATES LEADING TO HYDROCHLORIDE OF [4- (5-AMINomethyl-2-FLUORO-PHENYL) -PIPERIDIN-1-IL] - (4-BROMO-3-METHYL-5-PROPOXY-THIOFEN-2- IL) -METANONEInfo
- Publication number
- PE20071148A1 PE20071148A1 PE2007000345A PE2007000345A PE20071148A1 PE 20071148 A1 PE20071148 A1 PE 20071148A1 PE 2007000345 A PE2007000345 A PE 2007000345A PE 2007000345 A PE2007000345 A PE 2007000345A PE 20071148 A1 PE20071148 A1 PE 20071148A1
- Authority
- PE
- Peru
- Prior art keywords
- methyl
- compound
- formula
- thiofen
- piperidin
- Prior art date
Links
- -1 5-AMINomethyl-2-FLUORO-PHENYL Chemical class 0.000 title abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title 1
- 239000000543 intermediate Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 4
- 239000002904 solvent Substances 0.000 abstract 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 abstract 1
- QPLPMPAMOJIAMN-UHFFFAOYSA-N 3-oxobutanethioic s-acid Chemical compound CC(=O)CC(O)=S QPLPMPAMOJIAMN-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- KOOADCGQJDGAGA-UHFFFAOYSA-N [amino(dimethyl)silyl]methane Chemical compound C[Si](C)(C)N KOOADCGQJDGAGA-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000003973 alkyl amines Chemical class 0.000 abstract 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 150000003840 hydrochlorides Chemical class 0.000 abstract 1
- 230000002757 inflammatory effect Effects 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 abstract 1
- 150000004702 methyl esters Chemical class 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/20—Esters of monothiocarboxylic acids
- C07C327/22—Esters of monothiocarboxylic acids having carbon atoms of esterified thiocarboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
SE REFIERE A UN PROCEDIMIENTO DE PREPARACION DE COMPUESTOS INTERMEDIOS DE HIDROCLORURO DE [4-(5-AMINOMETIL-2-FLUORO-FENIL)-PIPERIDIN-1-IL]-(4-BROMO-3-METIL-5-PROPOXI-TIOFEN-2-IL)-METANONA TAL COMO: A) UN COMPUESTO DE FORMULA (8) O ESTER O-PROPILICO DEL ACIDO 3-OXO-TIOBUTIRICO QUE COMPRENDE CONDENSAR UN COMPUESTO DE FORMULA (7) CON ACETONA EN PRESENCIA DE UN DISOLVENTE ETEREO TAL COMO TETRAHIDROFURANO, 2-METILTETRAHIDROFURANO O TERC-BUTIL METIL ETER, UN DISOLVENTE HIDROCARBONADO TAL COMO TOLUENO O HEPTANO, Y UNA BASE METALICA ORGANICA TAL COMO (BIS)TRIMETILSILIL AMIDA DE SODIO, A UNA TEMPERATURA DE 15ºC A 55 ºC; Y B) UN COMPUESTO DE FORMULA (13) O ESTER METILICO DEL ACIDO (3-OXO-1-PROPOXI-BUT-1-ENILSULFANIL)-ACETICO QUE COMPRENDE ALQUILAR EL COMPUESTO DE FORMULA (8) CON BROMOACETATO DE METILO EN PRESENCIA DE UN DISOLVENTE APROTICO POLAR TAL COMO DIMETILFORMAMIDA, UN DISOLVENTE ETEREO, UN DISOLVENTE HIDROCARBONADO CLORADO TAL COMO DICLOROMETANO Y UNA BASE ALQUILAMINA TAL COMO TRIETILAMINA, A UNA TEMPERATURA DE 0ºC A 50 ºC. EL HIDROCLORURO DE [4-(5-AMINOMETIL-2-FLUORO-FENIL)-PIPERIDIN-1-IL]-(4-BROMO-3-METIL-5-PROPOXI-TIOFEN-2-IL)-METANONA ES UN INHIBIDOR DE TRIPTASA SIENDO UTIL EN EL TRATAMIENTO DE AFECCIONES INFLAMATORIASIT REFERS TO A PROCEDURE FOR THE PREPARATION OF INTERMEDIATE HYDROCHLORIDE COMPOUNDS OF [4- (5-AMINOMETHYL-2-FLUORO-PHENYL) -PIPERIDIN-1-IL] - (4-BROMO-3-METHYL-5-PROPOXI-THIOFEN- 2-IL) -METANONE SUCH AS: A) A COMPOUND OF FORMULA (8) OR O-PROPYL ESTER OF 3-OXO-THIOBUTYRIC ACID WHICH INCLUDES CONDENSING A COMPOUND OF FORMULA (7) WITH ACETONE IN THE PRESENCE OF AN ETEREO SOLVENT SUCH AS TETRAHYDROFURAN, 2-METHYLTETRAHYDROFURAN OR TERC-BUTYL METHYL ETHER, A HYDROCARBON SOLVENT SUCH AS TOLUENE OR HEPTANE, AND AN ORGANIC METALLIC BASE SUCH AS SODIUM (BIS) TRIMETHYLSILYL AMIDE, AT A TEMPERATURE OF 15ºC AT 55ºC. AND B) A COMPOUND OF FORMULA (13) OR METHYL ESTER OF ACID (3-OXO-1-PROPOXI-BUT-1-ENYLSULFANIL) -ACETIC THAT INCLUDES RENTING THE COMPOUND OF FORMULA (8) WITH METHYL BROMOACETATE IN THE PRESENCE OF A DISSOLVED POLAR APROTICO SUCH AS DIMETHYLFORMAMIDE, AN ETEREO SOLVENT, A CHLORINATED HYDROCARBON SOLVENT SUCH AS DICHLOROMETHANE AND AN ALKYLAMINE BASE SUCH AS TRIETHYLAMINE, AT A TEMPERATURE OF 0ºC TO 50ºC. [4- (5-AMINOMETHYL-2-FLUORO-PHENYL) -PIPERIDIN-1-IL] - (4-BROMO-3-METHYL-5-PROPOXY-THIOFEN-2-IL) -METHANONE HYDROCHLORIDE IS AN INHIBITOR OF TRIPTASE BEING USEFUL IN THE TREATMENT OF INFLAMMATORY AFFECTIONS
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US74390806P | 2006-03-29 | 2006-03-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PE20071148A1 true PE20071148A1 (en) | 2007-12-10 |
Family
ID=38283355
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PE2007000345A PE20071148A1 (en) | 2006-03-29 | 2007-03-27 | IMPROVEMENTS IN THE PREPARATION OF INTERMEDIATES LEADING TO HYDROCHLORIDE OF [4- (5-AMINomethyl-2-FLUORO-PHENYL) -PIPERIDIN-1-IL] - (4-BROMO-3-METHYL-5-PROPOXY-THIOFEN-2- IL) -METANONE |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP2001839A1 (en) |
| CN (1) | CN101405262A (en) |
| AR (1) | AR060181A1 (en) |
| MX (1) | MX2008011259A (en) |
| PE (1) | PE20071148A1 (en) |
| TW (1) | TW200811093A (en) |
| UY (1) | UY30247A1 (en) |
| WO (1) | WO2007118010A1 (en) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DOP2005000039A (en) * | 2004-03-26 | 2005-10-31 | Aventis Pharma Inc | HYDROCHLORIDE OF [4- (5-AMINOMETIL-2-FLUORO-PHENYL) - PIPERIDIN-1-IL] - (4-BOMO-3-METHYL-5-PROPOXI-TIOFEN-2-IL) -METANONE AS AN INHIBITOR OF THE MASTOCYT TRIPTASE |
-
2007
- 2007-03-27 PE PE2007000345A patent/PE20071148A1/en not_active Application Discontinuation
- 2007-03-28 EP EP07759555A patent/EP2001839A1/en not_active Withdrawn
- 2007-03-28 CN CNA2007800096074A patent/CN101405262A/en active Pending
- 2007-03-28 MX MX2008011259A patent/MX2008011259A/en not_active Application Discontinuation
- 2007-03-28 WO PCT/US2007/065339 patent/WO2007118010A1/en active Application Filing
- 2007-03-28 AR ARP070101299A patent/AR060181A1/en not_active Application Discontinuation
- 2007-03-29 UY UY30247A patent/UY30247A1/en not_active Application Discontinuation
- 2007-03-29 TW TW096110910A patent/TW200811093A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP2001839A1 (en) | 2008-12-17 |
| WO2007118010A1 (en) | 2007-10-18 |
| UY30247A1 (en) | 2007-11-30 |
| TW200811093A (en) | 2008-03-01 |
| AR060181A1 (en) | 2008-05-28 |
| CN101405262A (en) | 2009-04-08 |
| MX2008011259A (en) | 2008-09-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA | Abandonment or withdrawal |