AR116934A1 - Derivados de piperazinil y piperidinil-quinazolin-4(3h)-ona que tienen actividad contra el dolor - Google Patents
Derivados de piperazinil y piperidinil-quinazolin-4(3h)-ona que tienen actividad contra el dolorInfo
- Publication number
- AR116934A1 AR116934A1 ARP190103164A ARP190103164A AR116934A1 AR 116934 A1 AR116934 A1 AR 116934A1 AR P190103164 A ARP190103164 A AR P190103164A AR P190103164 A ARP190103164 A AR P190103164A AR 116934 A1 AR116934 A1 AR 116934A1
- Authority
- AR
- Argentina
- Prior art keywords
- substituted
- unsubstituted
- hydrogen
- alkynyl
- alkenyl
- Prior art date
Links
- LDRDHYQDRVRUPE-UHFFFAOYSA-N 2-piperidin-1-yl-1h-quinazolin-4-one Chemical class N1C2=CC=CC=C2C(=O)N=C1N1CCCCC1 LDRDHYQDRVRUPE-UHFFFAOYSA-N 0.000 title abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 14
- 239000001257 hydrogen Substances 0.000 abstract 14
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 12
- 150000002431 hydrogen Chemical group 0.000 abstract 12
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 11
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 11
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 6
- 229910052736 halogen Inorganic materials 0.000 abstract 5
- 150000002367 halogens Chemical class 0.000 abstract 5
- 229910052799 carbon Inorganic materials 0.000 abstract 4
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 3
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 abstract 3
- 150000001721 carbon Chemical group 0.000 abstract 3
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 3
- 125000004438 haloalkoxy group Chemical group 0.000 abstract 3
- 125000001188 haloalkyl group Chemical group 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 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 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- -1 -OR21 Chemical group 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000009977 dual effect Effects 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-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
- 125000004193 piperazinyl group Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000012453 solvate Substances 0.000 abstract 1
- 102000038650 voltage-gated calcium channel activity Human genes 0.000 abstract 1
- 108091023044 voltage-gated calcium channel activity Proteins 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/10—Spiro-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
- C07D239/90—Oxygen atoms with acyclic radicals attached in position 2 or 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- 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
- C07D403/06—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 linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- C07D403/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- 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
-
- 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
- C07D471/12—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 three hetero rings
- C07D471/18—Bridged systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (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)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Derivados de piperazinil y piperidinil-quinazolin-4(3H)-ona que poseen particularmente actividad dual hacia tanto la subunidad a₂d-1 del canal de calcio dependiente del voltaje como también hacia el receptor opioideo m (MOR). Se proveen también un método de preparación de éstos derivados, composiciones farmacéuticas que los comprenden y su uso para el tratamiento del dolor. Reivindicación 1: Compuesto de fórmula general (1), en la que Y¹ es -C(RʸRʸ)-; en el que Rʸ y Rʸ se seleccionan independientemente de hidrógeno, alquilo C₁₋₆ sustituido o no sustituido, alquenilo C₂₋₆ sustituido o no sustituido y alquinilo C₂₋₆ sustituido o no sustituido; alternativamente, Rʸ y Rʸ forman, con el átomo de carbono al que se unen, un cicloalquilo sustituido o no sustituido; Y² es -C(RʸRʸ)-; en el que Rʸ y Rʸ se seleccionan independientemente de hidrógeno, alquilo C₁₋₆ sustituido o no sustituido, alquenilo C₂₋₆ sustituido o no sustituido y alquinilo C₂₋₆ sustituido o no sustituido; alternativamente, Rʸ y Rʸ forman, con el átomo de carbono al que se unen, un cicloalquilo sustituido o no sustituido; Y³ es -CH₃ o -CH₂CH₃; alternativamente, Y² e Y³ tomados juntos, forman un cicloalquilo sustituido o no sustituido; W es nitrógeno o -CRʷ-; en el que Rʷ es hidrógeno o halógeno; alternativamente, Rʷ y uno de R⁵, R⁵, R⁵ o R⁵ forman un doble enlace: w¹, w², w³ y w⁴ se seleccionan independientemente del grupo que consiste en nitrógeno y carbono; R¹ se selecciona del grupo que consiste en hidrógeno, halógeno, alquilo C₁₋₆ sustituido o no sustituido, alquenilo C₂₋₆ sustituido o no sustituido, alquinilo C₂₋₆ sustituido o no sustituido, -OR⁸, -(CH₂)ₙNR⁸R⁸, -CH(fenil)-NR⁸R⁸, -NR⁸C(O)R⁸, -NR⁸C(O)OR⁸, -C(O)NR⁸R⁸, -C(O)OR⁸, -OCHR⁸R⁸, haloalquilo, haloalcoxilo, -CN, cicloalquilo sustituido o no sustituido, heterociclilo sustituido o no sustituido, arilo sustituido o no sustituido, alquilcicloalquilo sustituido o no sustituido, alquilheterociclilo sustituido o no sustituido y alquilarilo sustituido o no sustituido; n es 0, 1, 2, 3, 4 ó 5; R⁸ y R⁸ se seleccionan independientemente del grupo que consiste en hidrógeno, alquilo C₁₋₆ sustituido o no sustituido, alquenilo C₂₋₆ sustituido o no sustituido, alquinilo C₂₋₆ sustituido o no sustituido, cicloalquilo sustituido o no sustituido, heterociclilo sustituido o no sustituido, arilo sustituido o no sustituido, alquilcicloalquilo sustituido o no sustituido, alquilheterociclilo sustituido o no sustituido y alquilarilo sustituido o no sustituido; R² se selecciona de hidrógeno, halógeno, alquilo C₁₋₆ sustituido o no sustituido, alquenilo C₂₋₆ sustituido o no sustituido, alquinilo C₂₋₆ sustituido o no sustituido, -OR²¹, -NO₂, -NR²¹R²¹, -NR²¹C(O)R²¹, -NR²¹S(O)₂R²¹, -S(O)₂NR²¹R²¹, -NR²¹C(O)NR²¹R²¹, -SR²¹, -S(O)R²¹, -S(O)₂R²¹, -CN, haloalquilo, haloalcoxilo, -C(O)OR²¹, -C(O)NR²¹R²¹, -NR²¹S(O)₂NR²¹R²¹ y -C(CH₃)₂OR²¹; en los que R²¹, R²¹ y R²¹ se seleccionan independientemente de hidrógeno, alquilo C₁₋₆ sustituido o no sustituido, alquenilo C₂₋₆ sustituido o no sustituido y alquinilo C₂₋₆ sustituido o no sustituido; R³ se selecciona de hidrógeno, halógeno, alquilo C₁₋₆ sustituido o no sustituido, alquenilo C₂₋₆ sustituido o no sustituido, alquinilo C₂₋₆ sustituido o no sustituido, -OR³¹, -NO₃, -NR³¹R³¹, -NR³¹C(O)R³¹, -NR³¹S(O)₃R³¹, -S(O)₃NR³¹R³¹, -NR³¹C(O)NR³¹R³¹, -SR³¹, -S(O)R³¹, -S(O)₃R³¹, -CN, haloalquilo, haloalcoxilo, -C(O)OR³¹, -C(O)NR³¹R³¹, -NR³¹S(O)₃NR³¹R³¹ y -C(CH₃)₃OR³¹; en los que R³¹, R³¹ y R³¹ se seleccionan independientemente de hidrógeno, alquilo C₁₋₆ sustituido o no sustituido, alquenilo C₃₋₆ sustituido o no sustituido y alquinilo C₃₋₆ sustituido o no sustituido; R⁴ se selecciona de alquilo C₁₋₆ sustituido o no sustituido, alquenilo C₂₋₆ sustituido o no sustituido, alquinilo C₂₋₆ sustituido o no sustituido, cicloalquilo sustituido o no sustituido, alquilheterociclilo sustituido o no sustituido, alquilarilo sustituido o no sustituido y alquilcicloalquilo sustituido o no sustituido; R⁵, R⁵, R⁵ y R⁵ se seleccionan independientemente de hidrógeno, halógeno, alquilo C₁₋₆ sustituido o no sustituido, alquenilo C₂₋₆ sustituido o no sustituido y alquinilo C₂₋₆ sustituido o no sustituido; alternativamente, R⁵ y R⁵ y/o R⁵ y R⁵ tomados juntos con el átomo de carbono al que se unen forman un grupo carbonilo; R⁶, R⁶, R⁶ y R⁶ se seleccionan independientemente de hidrógeno, alquilo C₁₋₆ sustituido o no sustituido, alquenilo C₂₋₆ sustituido o no sustituido y alquinilo C₂₋₆ sustituido o no sustituido; R⁷ se selecciona de hidrógeno, alquilo C₁₋₆ sustituido o no sustituido, alquenilo C₂₋₆ sustituido o no sustituido y alquinilo C₂₋₆ sustituido o no sustituido; con la condición de que cuando R⁷ no es hidrógeno, entonces uno de R⁶, R⁶, R⁶ y R⁶ no es hidrógeno; opcionalmente en forma de uno de los estereoisómeros, preferiblemente enantiómeros o diastereómeros, un racemato o en forma de una mezcla de al menos dos de los estereoisómeros, preferiblemente enantiómeros y/o diastereómeros, en cualquier razón de mezclado, o una sal correspondiente del mismo, o un solvato correspondiente del mismo.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP18382772 | 2018-10-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR116934A1 true AR116934A1 (es) | 2021-06-30 |
Family
ID=64426834
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP190103164A AR116934A1 (es) | 2018-10-31 | 2019-10-31 | Derivados de piperazinil y piperidinil-quinazolin-4(3h)-ona que tienen actividad contra el dolor |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20220002314A1 (es) |
| EP (1) | EP3873895A1 (es) |
| JP (1) | JP7249428B2 (es) |
| CN (1) | CN113260614A (es) |
| AR (1) | AR116934A1 (es) |
| CA (1) | CA3117860A1 (es) |
| MX (1) | MX2021004885A (es) |
| TW (1) | TWI824050B (es) |
| WO (1) | WO2020089400A1 (es) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112694485B (zh) * | 2020-09-10 | 2023-04-07 | 四川海品信医药科技有限公司 | 一种阿片受体激动剂噻吩类化合物及其制备方法 |
| TW202302599A (zh) * | 2021-03-18 | 2023-01-16 | 西班牙商塔拉森斯調節公司 | 新５，６，７，８—四氫吡啶并［４＇，３＇：４，５］噻吩并［２，３—ｄ］嘧啶—４（３Ｈ）—酮衍生物作為西格瑪配位基 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5053411A (en) * | 1989-04-20 | 1991-10-01 | Anaquest, Inc. | N-aryl-N-[4-(1-heterocyclicalkyl)piperidinyl]amides and pharmaceutical compositions and methods employing such compounds |
| AUPR201600A0 (en) | 2000-12-11 | 2001-01-11 | Fujisawa Pharmaceutical Co., Ltd. | Quinazolinone derivative |
| JP2005511581A (ja) * | 2001-11-07 | 2005-04-28 | メルク エンド カムパニー インコーポレーテッド | 有糸分裂キネシン阻害剤 |
| WO2004018058A2 (en) * | 2002-08-21 | 2004-03-04 | Cytokinetics, Inc. | Compounds, compositions, and methods |
| TN2016000203A1 (en) * | 2013-12-20 | 2017-10-06 | Esteve Labor Dr | Piperazine derivatives having multimodal activity against pain. |
| WO2018100048A1 (en) * | 2016-11-30 | 2018-06-07 | Laboratorios Del Dr. Esteve, S.A. | 2-phenyl-2h-pyrazolo[3,4-d]pyridazine derivatives having activity against pain |
| WO2020089397A1 (en) * | 2018-10-31 | 2020-05-07 | Esteve Pharmaceuticals, S.A. | Substituted quinazolin-4(3h)-one derivatives having multimodal activity against pain |
| AU2020362224A1 (en) * | 2019-10-10 | 2022-04-21 | Esteve Pharmaceuticals, S.A. | Homopiperazinyl and homopiperidinyl quinazolin-4(3h)-one derivatives having multimodal activity against pain |
| KR20230017828A (ko) * | 2020-05-27 | 2023-02-06 | 에스테베 파마슈티칼스 에스에이 | 통증에 대한 다중모드 활성을 갖는 피라졸로[1,5-a]피리미딘 유도체 |
-
2019
- 2019-10-31 US US17/290,747 patent/US20220002314A1/en not_active Abandoned
- 2019-10-31 WO PCT/EP2019/079846 patent/WO2020089400A1/en not_active Ceased
- 2019-10-31 JP JP2021547945A patent/JP7249428B2/ja active Active
- 2019-10-31 EP EP19800951.6A patent/EP3873895A1/en active Pending
- 2019-10-31 MX MX2021004885A patent/MX2021004885A/es unknown
- 2019-10-31 CA CA3117860A patent/CA3117860A1/en active Pending
- 2019-10-31 AR ARP190103164A patent/AR116934A1/es not_active Application Discontinuation
- 2019-10-31 TW TW108139378A patent/TWI824050B/zh not_active IP Right Cessation
- 2019-10-31 CN CN201980087679.3A patent/CN113260614A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US20220002314A1 (en) | 2022-01-06 |
| TWI824050B (zh) | 2023-12-01 |
| MX2021004885A (es) | 2021-09-10 |
| WO2020089400A1 (en) | 2020-05-07 |
| CA3117860A1 (en) | 2020-05-07 |
| JP7249428B2 (ja) | 2023-03-30 |
| EP3873895A1 (en) | 2021-09-08 |
| TW202035391A (zh) | 2020-10-01 |
| JP2022509434A (ja) | 2022-01-20 |
| CN113260614A (zh) | 2021-08-13 |
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