AR101050A1 - 6,7-DIHYDROPIRAZOLO COMPOUNDS [1,5-A] PIRAZIN-4 (5H) -ONA AND ITS USE AS NEGATIVE ALLERGIC MODULATORS OF MGLUR2 RECEIVERS - Google Patents
6,7-DIHYDROPIRAZOLO COMPOUNDS [1,5-A] PIRAZIN-4 (5H) -ONA AND ITS USE AS NEGATIVE ALLERGIC MODULATORS OF MGLUR2 RECEIVERSInfo
- Publication number
- AR101050A1 AR101050A1 ARP140102170A ARP140102170A AR101050A1 AR 101050 A1 AR101050 A1 AR 101050A1 AR P140102170 A ARP140102170 A AR P140102170A AR P140102170 A ARP140102170 A AR P140102170A AR 101050 A1 AR101050 A1 AR 101050A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- mono
- compounds
- haloalkyl
- poly
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 8
- 101150016175 Grm2 gene Proteins 0.000 title 1
- 102100036837 Metabotropic glutamate receptor 2 Human genes 0.000 title 1
- 230000000172 allergic effect Effects 0.000 title 1
- 208000010668 atopic eczema Diseases 0.000 title 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 12
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 5
- 125000005843 halogen group Chemical group 0.000 abstract 4
- 125000006682 monohaloalkyl group Chemical group 0.000 abstract 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 abstract 3
- -1 2-pyridinyl Chemical group 0.000 abstract 3
- 102000016193 Metabotropic glutamate receptors Human genes 0.000 abstract 3
- 108010010914 Metabotropic glutamate receptors Proteins 0.000 abstract 3
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 229940126662 negative allosteric modulator Drugs 0.000 abstract 2
- 125000006684 polyhaloalkyl group Polymers 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- GLQXAHBYDJPCHG-UHFFFAOYSA-N 6,7-dihydro-5h-pyrazolo[1,5-a]pyrazin-4-one Chemical class O=C1NCCN2N=CC=C12 GLQXAHBYDJPCHG-UHFFFAOYSA-N 0.000 abstract 1
- 150000001204 N-oxides Chemical class 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 102000006239 metabotropic receptors Human genes 0.000 abstract 1
- 108020004083 metabotropic receptors Proteins 0.000 abstract 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000012453 solvate Substances 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Derivados de 6,7-dihidropirazolo[1,5-a]pirazin-4(5H)-ona como moduladores alostéricos negativos (NAM) del receptor de glutamato metabotrópico subtipo 2 (mGluR2). También está dirigida a composiciones farmacéuticas que comprenden dichos compuestos, a procesos para preparar dichos compuestos y composiciones y al uso de dichos compuestos y composiciones para prevenir o tratar trastornos en los que está implicado el subtipo mGluR2 de receptores metabotrópicos. Reivindicación 1: Un compuesto de fórmula (1) o una forma estereoisomérica del mismo, donde R¹ es fenilo o 2-piridinilo, cada uno opcionalmente sustituido por uno o mas sustituyentes, cada uno independientemente seleccionado del grupo de halo, alquilo C₁₋₄, mono- o poli-haloalquilo C₁₋₄, -O-alquilo C₁₋₄, -alquil C₁₋₄-O-alquilo C₁₋₄, mono- o poli-haloalquil C₁₋₄oxi, -alquil C₁₋₄-OH, alquil C₁₋₄tio, mono- o poli-haloalquil C₁₋₄tio, ciano, cicloalquilo C₃₋₇ opcionalmente sustituido por trifluorometilo y -SF₅; o es un resto de la fórmula (2); R² se selecciona de los compuestos de fórmula (3) y (4), en donde R⁵ y R⁶ se selecciona cada uno independientemente del grupo de hidrógeno, halo, ciano, alquilo C₁₋₄, -alquil C₁₋₄-OH, cicloalquilo C₃₋₇, mono- o poli-haloalquilo C₁₋₄, -alquil C₁₋₄-O-alquilo C₁₋₄, -O-alquilo C₁₋₄, mono- o poli-haloalquil C₁₋₄oxi, 1-acetilazetidin-3-ilo y NRR; en donde R se selecciona de hidrógeno y alquilo C₁₋₄; R se selecciona de hidrógeno y alquilo C₁₋₄; o R y R junto con el átomo de nitrógeno al que están unidos forman un grupo heterocíclico seleccionado del grupo de 1-azetidinilo, 1-pirrolidinilo, 1-piperidinilo, 1-piperazinilo y 4-morfolinilo; en donde cada uno de los grupos heterocíclicos puede sustituirse opcionalmente por un sustituyente que se selecciona de halo, hidroxilo, alquilo C₁₋₄, mono- o poli-haloalquilo C₁₋₄ y -(CO)alquilo C₁₋₄; R³ se selecciona de hidrógeno y alquilo C₁₋₄; R⁴ se selecciona del grupo de hidrógeno, alquilo C₁₋₄, mono- o poli-haloalquilo C₁₋₄, -alquil C₁₋₄-O-alquilo C₁₋₄ y -alquil C₁₋₄-OH; o un N-óxido, o una sal farmacéuticamente aceptable o un solvato del mismo. Reivindicación 15: Un compuesto de fórmula (5) en donde R²ᵃ es halo y R³ y R⁴ son tal como se definen en cualquiera de las reivindicaciones 1 a 6. Reivindicación 16: Un compuesto de acuerdo con la reivindicación 15 que tiene la fórmula (6).Derivatives of 6,7-dihydropyrazolo [1,5-a] pyrazin-4 (5H) -one as negative allosteric modulators (NAM) of the subbotot 2 metabotropic glutamate receptor (mGluR2). It is also directed to pharmaceutical compositions comprising said compounds, to processes for preparing said compounds and compositions and to the use of said compounds and compositions to prevent or treat disorders in which the mGluR2 subtype of metabotropic receptors is involved. Claim 1: A compound of formula (1) or a stereoisomeric form thereof, wherein R¹ is phenyl or 2-pyridinyl, each optionally substituted by one or more substituents, each independently selected from the group of halo, C₁₋₄ alkyl, mono- or poly-C₁₋₄-haloalkyl, -O-C₁₋₄-alkyl, -Cal-O-C₁₋₄-alkyl, mono- or poly-C₁₋₄oxy-alkyl-alkyl, -C₁₋₄-OH alkyl, alkyl C₁₋₄thio, mono- or poly-haloalkyl C₁₋₄thio, cyano, C₃₋₇ cycloalkyl optionally substituted by trifluoromethyl and -SF₅; or is a remainder of the formula (2); R² is selected from the compounds of formula (3) and (4), wherein R⁵ and R⁶ are each independently selected from the group of hydrogen, halo, cyano, C₁₋₄ alkyl, -C₁₋₄-OH alkyl, C₃ cycloalkyl ₋₇, mono- or C₁₋₄-haloalkyl, -C₁₋₄-O-C₁₋₄-alkyl, -O-C₁₋₄-alkyl, mono- or poly-haloxyC₁₋₄oxy, 1-acetylazetidine-3- ilo and NRR; wherein R is selected from hydrogen and C₁₋₄ alkyl; R is selected from hydrogen and C₁₋₄ alkyl; or R and R together with the nitrogen atom to which they are attached form a heterocyclic group selected from the group of 1-azetidinyl, 1-pyrrolidinyl, 1-piperidinyl, 1-piperazinyl and 4-morpholinyl; wherein each of the heterocyclic groups may optionally be substituted by a substituent selected from halo, hydroxyl, C₁₋₄ alkyl, mono- or poly-haloalkyl C₁₋₄ and - (CO) C alquilo alkyl; R³ is selected from hydrogen and C₁₋₄ alkyl; R⁴ is selected from the group of hydrogen, C₁₋₄ alkyl, mono- or C₁₋₄-haloalkyl, -C₁₋₄-O-C₁₋₄ alkyl and -C₁₋₄-OH alkyl; or an N-oxide, or a pharmaceutically acceptable salt or a solvate thereof. Claim 15: A compound of formula (5) wherein R²ᵃ is halo and R³ and R⁴ are as defined in any of claims 1 to 6. Claim 16: A compound according to claim 15 having the formula (6 ).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13170447 | 2013-06-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR101050A1 true AR101050A1 (en) | 2016-11-23 |
Family
ID=48536752
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP140102170A AR101050A1 (en) | 2013-06-04 | 2014-06-03 | 6,7-DIHYDROPIRAZOLO COMPOUNDS [1,5-A] PIRAZIN-4 (5H) -ONA AND ITS USE AS NEGATIVE ALLERGIC MODULATORS OF MGLUR2 RECEIVERS |
Country Status (1)
| Country | Link |
|---|---|
| AR (1) | AR101050A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111601811A (en) * | 2017-11-24 | 2020-08-28 | 大日本住友制药株式会社 | 6, 7-dihydropyrazolo [1,5-a ] pyrazinone derivatives and their pharmaceutical use |
-
2014
- 2014-06-03 AR ARP140102170A patent/AR101050A1/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111601811A (en) * | 2017-11-24 | 2020-08-28 | 大日本住友制药株式会社 | 6, 7-dihydropyrazolo [1,5-a ] pyrazinone derivatives and their pharmaceutical use |
| CN111601811B (en) * | 2017-11-24 | 2023-05-05 | 住友制药株式会社 | 6, 7-dihydropyrazolo [1,5-a ] pyrazinone derivatives and medical uses thereof |
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