AR085304A1 - Imidazo[5,1-f][1,2,4]triazinas para el tratamiento de trastornos neurologicos - Google Patents
Imidazo[5,1-f][1,2,4]triazinas para el tratamiento de trastornos neurologicosInfo
- Publication number
- AR085304A1 AR085304A1 ARP120100575A ARP120100575A AR085304A1 AR 085304 A1 AR085304 A1 AR 085304A1 AR P120100575 A ARP120100575 A AR P120100575A AR P120100575 A ARP120100575 A AR P120100575A AR 085304 A1 AR085304 A1 AR 085304A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- cycloalkyl
- heterocyclic
- independently selected
- group
- Prior art date
Links
- 208000012902 Nervous system disease Diseases 0.000 title 1
- 208000025966 Neurological disease Diseases 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 26
- 125000006647 (C3-C15) cycloalkyl group Chemical group 0.000 abstract 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 10
- 125000000623 heterocyclic group Chemical group 0.000 abstract 9
- 239000001257 hydrogen Substances 0.000 abstract 8
- 229910052739 hydrogen Inorganic materials 0.000 abstract 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 8
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- 125000000041 C6-C10 aryl group Chemical group 0.000 abstract 6
- 125000005843 halogen group Chemical group 0.000 abstract 6
- 125000001072 heteroaryl group Chemical group 0.000 abstract 6
- -1 -OR8 Chemical group 0.000 abstract 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 5
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 5
- 125000004043 oxo group Chemical group O=* 0.000 abstract 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 3
- 125000001424 substituent group Chemical group 0.000 abstract 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 abstract 1
- 125000006661 (C4-C6) heterocyclic group Chemical group 0.000 abstract 1
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 abstract 1
- 206010012289 Dementia Diseases 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 241000124008 Mammalia Species 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 210000003169 central nervous system Anatomy 0.000 abstract 1
- 208000010877 cognitive disease Diseases 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 239000011737 fluorine Chemical group 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 201000000980 schizophrenia Diseases 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
-
- 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
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
La presente se refiere a compuestos de fórmula (1) y a sales de los mismos farmacéuticamente aceptables, a procedimientos para la preparación de, a intermedios usados en la preparación de, y composiciones que contienen dichos compuestos y a los usos de dichos compuestos como un procedimiento para el tratamiento, de una enfermedad o afección seleccionada del grupo que consiste en trastornos del sistema nervioso central, trastornos cognitivos, esquizofrenia, demencia y otros trastornos, en un mamífero.Reivindicación 1: Un compuesto de fórmula (1) o una sal farmacéuticamente aceptable del mismo, en la que: “-A-R5” es un compuesto de fórmula (2), (3) ó (4); R1 es hidrógeno, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-15, -alquil C1-6-OH, -alquil C1-6-CN, -SF5, -CF3, -CHF2 o -CH2F; R2 es -alquil C1-6-R9, -NHR3, -N(R3)2, -O-alquil C1-6-R9, -OR8, cicloalquilo C3-15, arilo C6-10, heterocíclico C1-14 o heteroarilo C1-14; en los que dichos cicloalquilo C3-15 y heterocíclico C1-14 pueden contener opcionalmente un doble o triple enlace y de uno a dos grupos oxo (O=); y en los que dichos restos -alquil C1-6-R9, -NHR3, -N(R3)2, -O-alquil C1-6-R9, -OR8, cicloalquilo C3-15, arilo C6-10, heterocíclico C1-14 o heteroarilo C1-14 pueden estar opcionalmente sustituidos con de uno a tres sustituyentes seleccionados independientemente entre alquilo C1-6, alcoxi C1-6, halo y -CF3; cada R3 se selecciona independientemente entre el grupo que consiste en -alquil C1-6-R9, -alquenil C2-6-R9, -alquinil C2-6-R9 y -cicloalquil C3-15-R9, o cuando R2 es -N(R3)2 ambos de dichos R3 pueden tomarse junto con el átomo de nitrógeno al que están unidos para formar un anillo heterocíclico de 4 a 6 miembros que contiene opcionalmente uno o dos grupos oxo (O=) y están opcionalmente sustituidos con de uno a tres sustituyentes seleccionados independientemente entre el grupo que consiste en hidrógeno, flúor, -CN, -CF3, -CHF2, -CH2F, -OH, -O-alquilo C1-6, NH2, -NH-alquilo C1-6, -N[alquil C1-6]2, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, -(C=O)-R8, -(C=O)-OR8, -(C=O)-N(R8)2, -O-(C=O)-R8, -OR8, -O-(C=O)-OR8, -SR8, -S(O)R8, -S(O)2R8, -S(O)2N(R8)2, -NH-(C=O)-R8, -NH-(C=O)-OR8, -O-(C=O)-N(R8)2, -NH-(C=O)-N(R8)2, -N[alquil C1-6](C=O)-R8, -N[alquil C1-6](C=O)-OR8, -N[alquil C1-6](C=O)-N(R8)2, cicloalquilo C3-15, arilo C6-10, heterocíclico C1-14 y heteroarilo C1-14; en los que dichos cicloalquilo C3-15 y heterocíclico C1-14 pueden contener opcionalmente un doble o triple enlace y de uno a dos grupos oxo (O=); cada R4 se selecciona independientemente entre el grupo que consiste en hidrógeno, halo, alquilo C1-6, alquenilo C2-6, alquinilo C2-8, -CF3, -CHF2, -CH2F, o cicloalquilo C3-15; R4a es hidrógeno, alquilo C1-6, alquenilo C3-4, alquinilo C3-4, -CF3, -CHF2, -CH2F o cicloalquilo C3-15; R5 es un resto seleccionado del grupo de fórmulas (5), en las que n es 0,1, 2, 3 ó 4; cada R6 se selecciona independientemente entre el grupo que consiste en hidrógeno, halo, alquilo C1-6, -CF3, -CHF2, -CH2F, -CF2-alquilo C1-6, -SF5, -CN, -alquilo C1-6-CN, -NO2, -(C=O)-R8, -(C=O)-OR8, -OR8, -O-(C=O)-N(R8)2, -SR8, -S(O)R8, -S(O)2R8, NH2, -NH-alquilo C1-6, -N[alquil C1-6]2, -NH-(C=O)-R8, -NH-(C=O)-OR8, -N[alquil C1-6](C=O)-R8, -N[alquil C1-6](C=O)-OR8, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-15, heterocíclico C1-14, arilo C6-10 y heteroarilo C1-14; en los que dichos, cicloalquilo C3-15 y heterocíclico C1-14 pueden contener opcionalmente un doble o triple enlace y de uno a dos grupos oxo (O=); cada R7 se selecciona independientemente entre el grupo que consiste en hidrógeno, halo, alquilo C1-6, alquenilo C2-4, alquinilo C2-6, -CN, -CF3, -CHF2, -CH2F, -O-alquilo C1-6 y cicloalquilo C3-15; cada R8, siempre que aparezca, se selecciona independientemente entre el grupo que consiste en hidrógeno, alquilo C1-6, cicloalquilo C3-15, -CF3 y -CHF2; y cada R9 se selecciona independientemente entre el grupo que consiste en hidrógeno, halo, -CF3, -CHF2, -CH2F, -CF2-alquilo C1-6, -CN, -alquil C1-6-CN, -NO2, -(C=O)-R8, -(C=O)-OR8, -OR8, -O-(C=O)-N(R8)2, -SR8, -S(O)R8, -S(O)2R8, NH2, -NH-alquilo C1-6, -N[alquil C1-6]2, -NH-(C=O)-R8, -NH-(C=O)OR8, -N[alquil C1-6](CO)-R8, -N[alquil C1-6](C=O)-OR8, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-15, heterocíclico C1-14, arilo C6-10 y heteroarilo C1-14, en los que dichos, cicloalquilo C3-15 y heterocíclico C1-14 pueden contener opcionalmente un doble o triple enlace y de uno a dos grupos oxo (O=); y en los que cada uno de dichos restos cicloalquilo C3-15, heterocíclico C1-14, arilo C6-10 y heteroarilo C1-14 puede estar opcionalmente sustituido con de uno a tres sustituyentes seleccionados independientemente entre alquilo C1-6, alcoxi C1-6, halo y -CF3.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161445617P | 2011-02-23 | 2011-02-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR085304A1 true AR085304A1 (es) | 2013-09-18 |
Family
ID=45755439
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP120100575A AR085304A1 (es) | 2011-02-23 | 2012-02-22 | Imidazo[5,1-f][1,2,4]triazinas para el tratamiento de trastornos neurologicos |
Country Status (31)
| Country | Link |
|---|---|
| US (2) | US8598155B2 (es) |
| EP (1) | EP2681218A1 (es) |
| JP (1) | JP5543039B2 (es) |
| KR (1) | KR101548443B1 (es) |
| CN (1) | CN103391941A (es) |
| AP (1) | AP2013007070A0 (es) |
| AR (1) | AR085304A1 (es) |
| AU (1) | AU2012221828C1 (es) |
| BR (1) | BR112013021366A2 (es) |
| CA (1) | CA2825699A1 (es) |
| CL (1) | CL2013002125A1 (es) |
| CO (1) | CO6751271A2 (es) |
| CR (1) | CR20130371A (es) |
| CU (1) | CU20130107A7 (es) |
| DO (1) | DOP2013000194A (es) |
| EA (1) | EA022586B1 (es) |
| EC (1) | ECSP13012892A (es) |
| GT (1) | GT201300206A (es) |
| IL (1) | IL227716A0 (es) |
| MA (1) | MA34922B1 (es) |
| MX (1) | MX2013009684A (es) |
| NI (1) | NI201300071A (es) |
| PE (1) | PE20140236A1 (es) |
| PH (1) | PH12013501556A1 (es) |
| SG (1) | SG192576A1 (es) |
| TN (1) | TN2013000349A1 (es) |
| TW (1) | TWI469983B (es) |
| UA (1) | UA106692C2 (es) |
| UY (1) | UY33916A (es) |
| WO (1) | WO2012114222A1 (es) |
| ZA (1) | ZA201306348B (es) |
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|---|---|---|---|---|
| PH12013501556A1 (en) * | 2011-02-23 | 2017-10-25 | Pfizer | IMIDAZO[5,1-f][1,2,4]TRIAZINES FOR THE TREATMENT OF NEUROLOGICAL DISORDERS |
| US20140206667A1 (en) | 2012-11-14 | 2014-07-24 | Michela Gallagher | Methods and compositions for treating schizophrenia |
| TN2015000490A1 (fr) | 2013-05-02 | 2017-04-06 | Pfizer | Dérivés d'imidazo-triazine servant d' inhibiteurs de pde10 |
| US9815796B2 (en) | 2013-12-23 | 2017-11-14 | Merck Sharp & Dohme Corp. | Pyrimidone carboxamide compounds as PDE2 inhibitors |
| JP6696904B2 (ja) | 2014-01-08 | 2020-05-20 | イントラ−セルラー・セラピーズ・インコーポレイテッドＩｎｔｒａ−Ｃｅｌｌｕｌａｒ Ｔｈｅｒａｐｉｅｓ， Ｉｎｃ． | 製剤および医薬組成物 |
| PT3597649T (pt) | 2014-04-23 | 2022-01-21 | Dart Neuroscience Llc | Composições contendo compostos substituidos de [1,2,4]triazolo[1,5-a] pirimidin-7il como inibidores de pde2 |
| EP3215508A1 (en) | 2014-11-05 | 2017-09-13 | Dart NeuroScience (Cayman) Ltd. | Substituted 5-methyl-[1, 2, 4]triazolo [1,5-a) pyrimidin-2-amine compounds as pde2 inhibitors |
| WO2016090380A1 (en) | 2014-12-06 | 2016-06-09 | Intra-Cellular Therapies, Inc. | Organic compounds |
| HK1244427A1 (zh) | 2014-12-06 | 2018-08-10 | Intra-Cellular Therapies, Inc. | 有机化合物 |
| CN104525240A (zh) * | 2014-12-10 | 2015-04-22 | 河北工业大学 | 硝酸铁作为催化剂在苯与羟胺盐反应一步法制苯胺反应中的应用方法 |
| JP2017538769A (ja) | 2014-12-22 | 2017-12-28 | ファイザー・インク | プロスタグランジンｅｐ３受容体の拮抗薬 |
| TWI713497B (zh) * | 2015-02-26 | 2020-12-21 | 南韓商愛思開生物製藥股份有限公司 | 咪唑并嘧啶及咪唑并三衍生物及包含該衍生物之醫藥組成物 |
| WO2016145614A1 (en) | 2015-03-17 | 2016-09-22 | Merck Sharp & Dohme Corp. | Triazolyl pyrimidinone compounds as pde2 inhibitors |
| US10287269B2 (en) | 2015-03-26 | 2019-05-14 | Merck Sharp & Dohme Corp. | Pyrazolyl pyrimidinone compounds as PDE2 inhibitors |
| WO2016179059A1 (en) | 2015-05-05 | 2016-11-10 | Merck Sharp & Dohme Corp. | Heteroaryl-pyrimidinone compounds as pde2 inhibitors |
| WO2016183741A1 (en) | 2015-05-15 | 2016-11-24 | Merck Sharp & Dohme Corp. | Pyrimidinone amide compounds as pde2 inhibitors |
| WO2016191935A1 (en) | 2015-05-29 | 2016-12-08 | Merck Sharp & Dohme Corp. | 6-alkyl dihydropyrazolopyrimidinone compounds as pde2 inhibitors |
| WO2016192083A1 (en) | 2015-06-04 | 2016-12-08 | Merck Sharp & Dohme Corp. | Dihydropyrazolopyrimidinone compounds as pde2 inhibitors |
| WO2016209749A1 (en) | 2015-06-25 | 2016-12-29 | Merck Sharp & Dohme Corp. | Substituted pyrazolo/imidazolo bicyclic compounds as pde2 inhibitors |
| WO2017004134A1 (en) * | 2015-06-29 | 2017-01-05 | Nimbus Iris, Inc. | Irak inhibitors and uses thereof |
| WO2017000277A1 (en) | 2015-07-01 | 2017-01-05 | Merck Sharp & Dohme Corp. | Substituted triazolo bicycliccompounds as pde2 inhibitors |
| WO2017000276A1 (en) * | 2015-07-01 | 2017-01-05 | Merck Sharp & Dohme Corp. | Bicyclic heterocyclic compounds as pde2 inhibitors |
| EP3371188B1 (en) * | 2015-11-02 | 2019-10-23 | Janssen Pharmaceutica NV | [1,2,4]triazolo[1,5-a]pyrimidin-7-yl compound |
| CN105669680B (zh) * | 2016-03-24 | 2018-02-23 | 南京药捷安康生物科技有限公司 | 吡咯并[2,1‑f][1,2,4]三嗪‑4(1H)‑酮衍生物类PDE9A抑制剂 |
| WO2018065288A1 (de) | 2016-10-07 | 2018-04-12 | Bayer Cropscience Aktiengesellschaft | 2-[2-phenyl-1-(sulfonylmethyl)vinyl]-imidazo[4,5-b]pyridin-derivate und verwandte verbindungen als schädlingsbekämpfungsmittel im pflanzenschutz |
| AU2017353315B2 (en) | 2016-11-02 | 2021-09-16 | Janssen Pharmaceutica Nv | (1,2,4)triazolo(1,5-a)pyrimidine compounds as PDE2 inhibitors |
| CN109890824B (zh) | 2016-11-02 | 2022-05-24 | 詹森药业有限公司 | 作为pde2抑制剂的[1,2,4]三唑并[1,5-a]嘧啶化合物 |
| TWI764950B (zh) | 2016-11-02 | 2022-05-21 | 比利時商健生藥品公司 | Ｐｄｅ２抑制劑 |
| UY37556A (es) | 2017-01-10 | 2018-07-31 | Bayer Ag | Derivados heterocíclicos como pesticidas |
| EP3568395A1 (de) | 2017-01-10 | 2019-11-20 | Bayer Aktiengesellschaft | Heterocyclen-derivate als schädlingsbekämpfungsmittel |
| EP3713572B1 (en) | 2017-11-23 | 2025-07-30 | Oslo University Hospital HF | Treatment of tachycardia |
| CN108640923A (zh) * | 2018-07-09 | 2018-10-12 | 湖南天地恒制药有限公司 | 一种托法替布关键中间体的制备方法 |
| WO2020086650A2 (en) * | 2018-10-23 | 2020-04-30 | Intra-Cellular Therapies, Inc. | Novel compounds |
| US11492362B1 (en) | 2022-02-17 | 2022-11-08 | King Abdulaziz University | Pyridine derivatives for the treatment of hyperproliferative diseases |
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| WO1993012113A1 (en) * | 1991-12-17 | 1993-06-24 | The Upjohn Company | 3-SUBSTITUTED IMIDAZO (1,5-a) AND IMIDAZO (1,5-a)-TRIAZOLO (1,5-c) QUINOXALINES AND QUINAZOLINES WITH CNS ACTIVITY |
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| US7683575B2 (en) | 2007-07-18 | 2010-03-23 | Tesla Motors, Inc. | Method and apparatus for identifying and disconnecting short-circuited battery cells within a battery pack |
| BRPI0910232A2 (pt) | 2008-03-19 | 2015-09-29 | Osi Pharm Inc | formas de sais inibidores do mtor |
| WO2009143051A1 (en) | 2008-05-19 | 2009-11-26 | Osi Pharmaceuticals, Inc. | Substituted imidazopyr-and imidazotri-azines |
| CA2764173A1 (en) | 2009-07-09 | 2011-01-13 | OSI Pharmaceuticals, LLC | Process for substituted 3-amino-5-oxo-4,5-dihydro-[1,2,4]triazines |
| BR112012019302B1 (pt) | 2010-02-03 | 2022-06-21 | Incyte Holdings Corporation | Imidazo[1,2-b] [1,2,4]triazinas como inibidores de c-met, composição que as compreende e métodos in vitro de inibir a atividade de c-met cinase, de inibir a via de sinalização da hgf/c-met cinase em uma célula e de inibir a atividade proliferativa de uma célula |
| PH12013501556A1 (en) * | 2011-02-23 | 2017-10-25 | Pfizer | IMIDAZO[5,1-f][1,2,4]TRIAZINES FOR THE TREATMENT OF NEUROLOGICAL DISORDERS |
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