AR096118A1 - Condensación de pirazol-amidas catalizadas con pd - Google Patents
Condensación de pirazol-amidas catalizadas con pdInfo
- Publication number
- AR096118A1 AR096118A1 ARP140101743A ARP140101743A AR096118A1 AR 096118 A1 AR096118 A1 AR 096118A1 AR P140101743 A ARP140101743 A AR P140101743A AR P140101743 A ARP140101743 A AR P140101743A AR 096118 A1 AR096118 A1 AR 096118A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- halogen
- nitrogen
- alkoxy
- formula
- Prior art date
Links
- 230000005494 condensation Effects 0.000 title 1
- 238000009833 condensation Methods 0.000 title 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 5
- 229910052757 nitrogen Inorganic materials 0.000 abstract 5
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 125000005842 heteroatom Chemical group 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- BNYCHCAYYYRJSH-UHFFFAOYSA-N 1h-pyrazole-5-carboxamide Chemical class NC(=O)C1=CC=NN1 BNYCHCAYYYRJSH-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000005234 imidazo[1,2-a]pyridines Chemical class 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- -1 phenylsulfonyloxy Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Reivindicación 1: Proceso de obtención de compuestos imidazo[1,2-a]-piridina de la fórmula (1) en la que: R¹ es alcoxi C₁₋₄ o NR⁴R⁵, en el que: R⁴ y R⁵ son con independencia hidrógeno o alquilo C₁₋₄ o R⁴ y R⁵ junto con el átomo de nitrógeno, al que están unidos, forman un anillo heterocíclico saturado de 4 a 6 eslabones, que puede contener uno o más heteroátomos elegidos entre nitrógeno y oxígeno; R² es alquilo C₁₋₄, (alcoxi C₁₋₄)carbonilo, halógeno, fenilo, que está opcionalmente sustituido por alquilo C₁₋₄, alcoxi C₁₋₄ o halógeno o es NR⁴R⁵ en el que: R⁴ y R⁵ son con independencia hidrógeno o alquilo C₁₋₄ o R⁴ y R⁵ junto con el átomo de nitrógeno, al que están unidos, forman un anillo heterocíclico saturado de 4 a 6 eslabones, que puede contener uno o más heteroátomos elegidos entre nitrógeno y oxígeno; R³ es alquilo C₁₋₄ y X es nitrógeno o CH; que consiste en la reacción de un derivado pirazol-carboxamida de la fórmula (2) en la que R¹ y R³ tienen los significados definidos antes; con un derivado halógeno-imidazo[1,2-a]piridina de Ia fórmula (3) en la que R² y X tienen los significados definidos antes e Y significa halógeno, (alquil C₁₋₄)-sulfoniloxi, mono- o poli-halógeno-(alquil C₁₋₄)-sulfoniloxi, mono- o poli-(alquil C₁₋₄)-fenilsulfoniloxi o fenilsulfoniloxi; en presencia de un catalizador de paladio, una base y un disolvente orgánico.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13166027 | 2013-04-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR096118A1 true AR096118A1 (es) | 2015-12-09 |
Family
ID=48190360
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP140101743A AR096118A1 (es) | 2013-04-30 | 2014-04-28 | Condensación de pirazol-amidas catalizadas con pd |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US9505759B2 (es) |
| EP (1) | EP2991984B1 (es) |
| JP (1) | JP2016520047A (es) |
| KR (1) | KR20160002839A (es) |
| CN (1) | CN105164126B (es) |
| AR (1) | AR096118A1 (es) |
| AU (1) | AU2014261512B2 (es) |
| BR (1) | BR112015026132A2 (es) |
| CA (1) | CA2909477A1 (es) |
| DK (1) | DK2991984T3 (es) |
| ES (1) | ES2622754T3 (es) |
| HK (1) | HK1213557A1 (es) |
| HU (1) | HUE032407T2 (es) |
| IL (1) | IL242032B (es) |
| MX (1) | MX2015014729A (es) |
| MY (1) | MY169128A (es) |
| PL (1) | PL2991984T3 (es) |
| RU (1) | RU2663834C2 (es) |
| SG (1) | SG11201508924XA (es) |
| SI (1) | SI2991984T1 (es) |
| WO (1) | WO2014177493A1 (es) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6568855B2 (ja) | 2014-07-30 | 2019-08-28 | 持田製薬株式会社 | ピラゾール誘導体の製造方法 |
| WO2016017719A1 (ja) * | 2014-07-30 | 2016-02-04 | 持田製薬株式会社 | ピラゾール誘導体の製造方法 |
| WO2020021024A1 (en) * | 2018-07-26 | 2020-01-30 | Phenex Pharmaceuticals Ag | Substituted bicyclic compounds as modulators of the aryl hydrocarbon receptor (ahr) |
| CA3180793A1 (en) | 2020-06-05 | 2021-12-09 | George GARIBALDI | Use of a phosphodiesterase 10 inhibitor for the treatment of tourette syndrome |
| WO2023164178A2 (en) * | 2022-02-25 | 2023-08-31 | Journey Colab Corp. | Methods for preparing mescaline |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE0102808D0 (sv) * | 2001-08-22 | 2001-08-22 | Astrazeneca Ab | New compounds |
| MY147647A (en) * | 2005-03-21 | 2012-12-31 | S Bio Pte Ltd | Imidazo [1,2-a] pyridine derivatives : preparation and pharmaceutical applications |
| WO2011036127A1 (en) * | 2009-09-24 | 2011-03-31 | F. Hoffmann-La Roche Ag | Imidazopyridine or imidazopyrimidine derivatives as phosphodiesterase 10a inhibitors |
| US8349824B2 (en) | 2010-12-07 | 2013-01-08 | Hoffmann-La Roche Inc. | Triazolopyridine compounds |
| KR101778354B1 (ko) * | 2011-08-18 | 2017-09-13 | 니뽄 신야쿠 가부시키가이샤 | 헤테로환 유도체 및 의약 |
| WO2013041472A1 (en) * | 2011-09-19 | 2013-03-28 | F. Hoffmann-La Roche Ag | Triazolopyridine compounds as pde10a inhibitors |
-
2014
- 2014-04-28 SG SG11201508924XA patent/SG11201508924XA/en unknown
- 2014-04-28 ES ES14719769.3T patent/ES2622754T3/es active Active
- 2014-04-28 MX MX2015014729A patent/MX2015014729A/es unknown
- 2014-04-28 BR BR112015026132A patent/BR112015026132A2/pt not_active Application Discontinuation
- 2014-04-28 SI SI201430204A patent/SI2991984T1/sl unknown
- 2014-04-28 MY MYPI2015002659A patent/MY169128A/en unknown
- 2014-04-28 HU HUE14719769A patent/HUE032407T2/en unknown
- 2014-04-28 AR ARP140101743A patent/AR096118A1/es unknown
- 2014-04-28 AU AU2014261512A patent/AU2014261512B2/en not_active Ceased
- 2014-04-28 WO PCT/EP2014/058549 patent/WO2014177493A1/en active Application Filing
- 2014-04-28 EP EP14719769.3A patent/EP2991984B1/en not_active Not-in-force
- 2014-04-28 CN CN201480024745.XA patent/CN105164126B/zh not_active Expired - Fee Related
- 2014-04-28 KR KR1020157030741A patent/KR20160002839A/ko not_active Application Discontinuation
- 2014-04-28 RU RU2015145721A patent/RU2663834C2/ru not_active IP Right Cessation
- 2014-04-28 JP JP2016511026A patent/JP2016520047A/ja not_active Ceased
- 2014-04-28 CA CA2909477A patent/CA2909477A1/en not_active Abandoned
- 2014-04-28 PL PL14719769T patent/PL2991984T3/pl unknown
- 2014-04-28 DK DK14719769.3T patent/DK2991984T3/en active
-
2015
- 2015-10-12 IL IL242032A patent/IL242032B/en not_active IP Right Cessation
- 2015-10-28 US US14/925,544 patent/US9505759B2/en not_active Expired - Fee Related
-
2016
- 2016-02-11 HK HK16101489.8A patent/HK1213557A1/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU2014261512B2 (en) | 2017-10-05 |
| KR20160002839A (ko) | 2016-01-08 |
| DK2991984T3 (en) | 2017-05-08 |
| CA2909477A1 (en) | 2014-11-06 |
| RU2663834C2 (ru) | 2018-08-10 |
| SG11201508924XA (en) | 2015-11-27 |
| CN105164126A (zh) | 2015-12-16 |
| BR112015026132A2 (pt) | 2017-07-25 |
| HUE032407T2 (en) | 2017-09-28 |
| MX2015014729A (es) | 2016-03-07 |
| EP2991984A1 (en) | 2016-03-09 |
| ES2622754T3 (es) | 2017-07-07 |
| AU2014261512A1 (en) | 2015-10-15 |
| US9505759B2 (en) | 2016-11-29 |
| RU2015145721A (ru) | 2017-06-07 |
| WO2014177493A1 (en) | 2014-11-06 |
| CN105164126B (zh) | 2017-05-31 |
| PL2991984T3 (pl) | 2017-07-31 |
| US20160046628A1 (en) | 2016-02-18 |
| IL242032B (en) | 2018-06-28 |
| HK1213557A1 (zh) | 2016-07-08 |
| MY169128A (en) | 2019-02-18 |
| JP2016520047A (ja) | 2016-07-11 |
| SI2991984T1 (sl) | 2017-05-31 |
| EP2991984B1 (en) | 2017-03-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FB | Suspension of granting procedure |