PE20070114A1 - TUBULIN INHIBITOR AND PROCESS FOR ITS PREPARATION - Google Patents
TUBULIN INHIBITOR AND PROCESS FOR ITS PREPARATIONInfo
- Publication number
- PE20070114A1 PE20070114A1 PE2006000657A PE2006000657A PE20070114A1 PE 20070114 A1 PE20070114 A1 PE 20070114A1 PE 2006000657 A PE2006000657 A PE 2006000657A PE 2006000657 A PE2006000657 A PE 2006000657A PE 20070114 A1 PE20070114 A1 PE 20070114A1
- Authority
- PE
- Peru
- Prior art keywords
- trifluoro
- pirazin
- react
- phenyl
- give
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 2
- 229940122429 Tubulin inhibitor Drugs 0.000 title 1
- 239000002904 solvent Substances 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 abstract 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 abstract 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 2
- 239000000010 aprotic solvent Substances 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- SNMLKBMPULDPTA-REOHCLBHSA-N (2s)-1,1,1-trifluoropropan-2-amine Chemical compound C[C@H](N)C(F)(F)F SNMLKBMPULDPTA-REOHCLBHSA-N 0.000 abstract 1
- -1 METHYLAMINO Chemical class 0.000 abstract 1
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- 102000004243 Tubulin Human genes 0.000 abstract 1
- 108090000704 Tubulin Proteins 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 201000011510 cancer Diseases 0.000 abstract 1
- 239000012320 chlorinating reagent Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000001530 fumaric acid Substances 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
SE REFIERE AL COMPUESTO HEMIFUMARATO DE 6-CLORO-5-{2,6-DIFLUORO-4-[3-(METILAMINO)PROPOXI]FENIL}-2-PIRAZIN-2-IL-N-[(1S)-2,2,2-TRIFLUORO-1-METILETIL]PIRIMIDIN-4-AMINA Y SU PROCEDIMIENTO DE PREPARACION QUE CONSISTE EN: A) HACER REACCIONAR UN PIRAZINO-2-CARBONITRILOEN UNA BASE A EN UN ALCOHOL Y TRATAR CON UNA SAL DE AMONIO DE UN ACIDO INORGANICO PARA DAR UNA SAL DE ACIDO PIRAZINO-2-CARBOXIAMIDINA INORGANICA (A); B) HACER REACCIONAR (A) CON UN ESTER DE ACIDO MALONICO DE FORMULA I, DONDE R1 Y R2 SON CADA UNO ALQUILO C1-C3 EN UN SOLVENTE APROTICO EN PRESENCIA DE UNA BASE Y ACIDIFICAR PARA OBTENER 2-PIRAZIN-2-IL-5-(2,4,6-TRIFLUORO-FENIL)-PIRIMIDINO-4,6-DIOL (B); C) CLORINAR (B) CON OXICLORURO FOSFOROSO COMO REACTIVO DE CLORINACION EN PRESENCIA DE UNA AMINA BASE EN UN SOLVENTE APROTICO PARA DAR 4,6-DICLORO-2-PIRAZIN-2-IL-5-(2,4,6-TRIFLUORO-FENIL)-PIRIMIDINA (C); D) HACER REACCIONAR (C) CON (S)-2,2,2-TRIFLUORO-1-METIL-ETILAMINA EN UN SOLVENTE APROTICO PARA DAR 6-CLORO-2-PIRAZIN-2-IL-N-[(1S)-2,2,2-TRIFLUORO-1-METILETIL]-5-(2,4,6-TRIFLUOROFENIL)PIRIMIDIN-4-AMINA (D); E) HACER REACCIONAR 3-METILAMINO-PROPAN-1-OL CONBASE BEN UN SOLVENTE APROTICO Y ADICIONAR (D) PARA DAR 6-CLORO-5-{2,6-DIFLUORO-4-[3-(METILAMINO)PROPOXI]FENIL}-2-IL-N-[(1S)-2,2,2-TRIFLUORO-1-METILETIL]PIRIMIDIN-4-AMINA (E); F) HACER REACCIONAR (E) EN UN SOLVENTE APROTICO CON ACIDO FUMARICO EN UN ALCOHOL PARA OBTENER DICHO HEMIFUMARATO, EL CUAL ES UN INHIBIDOR DE TUBULINA UTIL EN EL TRATAMIENTO DE CANCERREFERS TO THE HEMIFUMARATE COMPOUND OF 6-CHLORO-5- {2,6-DIFLUORO-4- [3- (METHYLAMINO) PROPOXI] PHENYL} -2-PIRAZIN-2-IL-N - [(1S) -2.2 , 2-TRIFLUORO-1-METHYLETHYL] PYRIMIDIN-4-AMINE AND ITS PREPARATION PROCEDURE WHICH CONSISTS OF: A) REACTING A PIRAZINE-2-CARBONITRILE IN A BASE IN AN ALCOHOL AND TREATING WITH AN AMMONIUM SALT OF AN INORGANIC ACID TO GIVE A SALT OF INORGANIC PIRAZINE-2-CARBOXIAMIDINE ACID (A); B) REACT (A) WITH AN ESTER OF MALONIC ACID OF FORMULA I, WHERE R1 AND R2 ARE EACH C1-C3 ALKYL IN AN APROTICAL SOLVENT IN THE PRESENCE OF A BASE AND ACIDIFY TO OBTAIN 2-PIRAZIN-2-IL-5 - (2,4,6-TRIFLUORO-PHENYL) -PYRIMIDINE-4,6-DIOL (B); C) CHLORINATING (B) WITH PHOSPHORUS OXYCHLORIDE AS A CHLORINATING REAGENT IN THE PRESENCE OF A BASE AMINE IN AN APROTICAL SOLVENT TO GIVE 4,6-DICHLORO-2-PIRAZIN-2-IL-5- (2,4,6-TRIFLUORO- PHENYL) -PYRIMIDINE (C); D) REACT (C) WITH (S) -2,2,2-TRIFLUORO-1-METHYL-ETHYLAMINE IN AN APROTICAL SOLVENT TO GIVE 6-CHLORO-2-PIRAZIN-2-IL-N - [(1S) - 2,2,2-TRIFLUORO-1-METHYLETHYL] -5- (2,4,6-TRIFLUOROPHENYL) PYRIMIDIN-4-AMINE (D); E) REACT 3-METHYLAMINE-PROPAN-1-OL WITH BASED BEN AN APROTIC SOLVENT AND ADD (D) TO GIVE 6-CHLORINE-5- {2,6-DIFLUORO-4- [3- (METHYLAMINE) PROPOXI] PHENYL} -2-IL-N - [(1S) -2,2,2-TRIFLUORO-1-METHYLETHYL] PYRIMIDIN-4-AMINE (E); F) REACT (E) IN AN APROTIC SOLVENT WITH FUMARIC ACID IN AN ALCOHOL TO OBTAIN SAID HEMIFUMARATE, WHICH IS A USEFUL INHIBITOR OF TUBULIN IN THE TREATMENT OF CANCER
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US69001605P | 2005-06-13 | 2005-06-13 | |
| US80278106P | 2006-05-24 | 2006-05-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PE20070114A1 true PE20070114A1 (en) | 2007-02-03 |
Family
ID=37074929
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PE2006000657A PE20070114A1 (en) | 2005-06-13 | 2006-06-13 | TUBULIN INHIBITOR AND PROCESS FOR ITS PREPARATION |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP1891052A1 (en) |
| JP (1) | JP2008543838A (en) |
| AR (1) | AR054392A1 (en) |
| AU (1) | AU2006259663A1 (en) |
| BR (1) | BRPI0612145A2 (en) |
| CA (1) | CA2610416A1 (en) |
| GT (1) | GT200600257A (en) |
| MX (1) | MX2007015718A (en) |
| PE (1) | PE20070114A1 (en) |
| SV (1) | SV2007002573A (en) |
| TW (1) | TW200716613A (en) |
| WO (1) | WO2006138180A1 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011057805A1 (en) | 2009-11-12 | 2011-05-19 | R&D Biopharmaceuticals Gmbh | Tubulin inhibitors |
| US9649317B2 (en) * | 2012-09-19 | 2017-05-16 | The Trustees Of The University Of Pennsylvania | Heterocyclic compounds and their use for the treatment of neurodegenerative tauopathies |
| WO2017181974A1 (en) * | 2016-04-20 | 2017-10-26 | 苏州苏领生物医药有限公司 | Five-membered heterocyclic compound, preparation method therefor, pharmaceutical composition and use |
| US11623927B2 (en) | 2018-03-02 | 2023-04-11 | The Trustees Of The University Of Pennsylvania | Substituted [1,2,4]triazolo[1,5-a]pyrimidines for stabilizing microtubules |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE432077T1 (en) * | 2003-09-24 | 2009-06-15 | Wyeth Corp | 5-ARYLPYRIMIDINE AS AN ANTI-CANCER AGENT |
| WO2005030775A1 (en) * | 2003-09-24 | 2005-04-07 | Wyeth Holdings Corporation | 6-[(substituted)phenyl]triazolopyrimidines as anticancer agents |
-
2006
- 2006-06-08 WO PCT/US2006/022574 patent/WO2006138180A1/en not_active Ceased
- 2006-06-08 BR BRPI0612145-4A patent/BRPI0612145A2/en not_active Application Discontinuation
- 2006-06-08 JP JP2008516956A patent/JP2008543838A/en not_active Withdrawn
- 2006-06-08 CA CA002610416A patent/CA2610416A1/en not_active Abandoned
- 2006-06-08 EP EP06784720A patent/EP1891052A1/en not_active Withdrawn
- 2006-06-08 MX MX2007015718A patent/MX2007015718A/en not_active Application Discontinuation
- 2006-06-08 AU AU2006259663A patent/AU2006259663A1/en not_active Abandoned
- 2006-06-12 TW TW095120855A patent/TW200716613A/en unknown
- 2006-06-12 AR ARP060102470A patent/AR054392A1/en unknown
- 2006-06-13 GT GT200600257A patent/GT200600257A/en unknown
- 2006-06-13 SV SV2006002573A patent/SV2007002573A/en not_active Application Discontinuation
- 2006-06-13 PE PE2006000657A patent/PE20070114A1/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2610416A1 (en) | 2006-12-28 |
| EP1891052A1 (en) | 2008-02-27 |
| TW200716613A (en) | 2007-05-01 |
| BRPI0612145A2 (en) | 2010-10-19 |
| AU2006259663A1 (en) | 2006-12-28 |
| JP2008543838A (en) | 2008-12-04 |
| SV2007002573A (en) | 2007-01-03 |
| AR054392A1 (en) | 2007-06-20 |
| GT200600257A (en) | 2007-02-14 |
| WO2006138180A1 (en) | 2006-12-28 |
| MX2007015718A (en) | 2008-02-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| PE20171102A1 (en) | PROCESSES FOR PREPARING JAK INHIBITORS AND RELATED INTERMEDIARY COMPOUNDS | |
| AR061924A1 (en) | PROCESS TO ELABORATE 2- AMINO -5 - HALOBENZAMIDS 3- REPLACED | |
| CO6220910A2 (en) | PROCESS FOR THE PRODUCTION OF PESTICIDE BENZAMID COMPOUNDS | |
| PE20071238A1 (en) | PROCESS FOR THE PREPARATION OF HYDROXY SUBSTITUTE HETEROCICLES | |
| AR077924A1 (en) | PROCESSES TO PREPARE PEMETREXED | |
| PE20230156A1 (en) | HYDROCHLORIC ACID SALTS OF (R)-4-(3-((S)-1-(4-AMINO-3-METHYL-1H PYRAZOLO[3,4-D]PYRIMIDIN-1-IL)ETHYL)-5- CHLORO-2-ETOXY-6-FLUOROPHENYL)PYRROLIDIN-2-ONE | |
| RU2013119617A (en) | METHOD FOR PRODUCING 2-AMINO-N- (2, 2, 2-TRIFTORETHYL) ACETAMIDE | |
| PE20120424A1 (en) | SUBSTITUTE QUINAZOLINE COMPOUNDS | |
| RU2012156217A (en) | METHOD FOR PRODUCING 5-SUBSTITUTED-8-ALCOXY [1,2,4] TRIAZOLO [1,5-c] PYRIMIDIN-2-AMINES | |
| EA201891769A1 (en) | METHOD OF OBTAINING A COMPOUND OF PYRROLO [3,2-d] PYRIMIDINE AND INTERMEDIATE COMPOUNDS | |
| CL2023000228A1 (en) | Processes for preparing 3-(2-pyrimidinyl)pyrazol derivatives | |
| PE20070114A1 (en) | TUBULIN INHIBITOR AND PROCESS FOR ITS PREPARATION | |
| GB0508717D0 (en) | Chemical compounds | |
| AR081399A1 (en) | PROCESS TO PREPARE A PIRIMIDINONE COMPOUND, INTERMEDIATE COMPOUNDS IN SUCH PROCESS AND PROCESSES TO REPAIR THEM. | |
| MX2019000138A (en) | NOVEL PROCESSES FOR PREPARATION OF SOLUBLE GUANILATE CYCLASE STIMULATORS. | |
| JP2019525913A5 (en) | ||
| DE602006013136D1 (en) | ERMEDIATE | |
| TW200745090A (en) | Chemical compounds | |
| Ma et al. | Unsymmetric monothiooxalamides from S8, bromodifluoro reagents and anilines: Synthesis and applications | |
| AR066430A1 (en) | PROCESS TO PREPARE AROMATASE INHIBITORS AND EXEMESTANE CRYSTAL FORM | |
| AR092563A1 (en) | PROCESS FOR THE PREPARATION OF 2-AMINO-5,8-DIMETOXI [1,2,4] TRIAZOL [1,5-c] PYRIMIDINE FROM 4-CHLORINE-2,5-DIMETOXIPIRIMIDINE | |
| EA200600542A1 (en) | METHOD FOR MANUFACTURE THIP | |
| AR058210A1 (en) | PROCEDURE FOR PREPARING 5-AMINO-3H-TIAZOLO [4,5-D] PIRIMIDIN-2-ONA, A USEFUL INTERMEDIARY FOR THE PREPARATION OF CERTAIN NUCLEOSIDS OF TIAZOLO [4,5-D] PYRIMIDINE THAT ACT AS IMMUNOMODULATORS. | |
| ATE465999T1 (en) | METHOD FOR PRODUCING SUBSTITUTED PYRIMIDINES | |
| ATE443053T1 (en) | QUINAZOLEIN DERIVATIVES USED AS INHIBITORS OF ERBB TYROSINKINASE |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FC | Refusal |