AR085099A1 - Derivados de (1,2,4)triazolo[4,3-a]quinoxalina como inhibidores de fosfodiesterasas - Google Patents
Derivados de (1,2,4)triazolo[4,3-a]quinoxalina como inhibidores de fosfodiesterasasInfo
- Publication number
- AR085099A1 AR085099A1 ARP120100303A ARP120100303A AR085099A1 AR 085099 A1 AR085099 A1 AR 085099A1 AR P120100303 A ARP120100303 A AR P120100303A AR P120100303 A ARP120100303 A AR P120100303A AR 085099 A1 AR085099 A1 AR 085099A1
- Authority
- AR
- Argentina
- Prior art keywords
- triazolo
- quinoxaline
- halo
- methyl
- optionally substituted
- Prior art date
Links
- QNSRYVDGWDXBHV-UHFFFAOYSA-N [1,2,4]triazolo[4,3-a]quinoxaline Chemical class C1=CC=C2N3C=NN=C3C=NC2=C1 QNSRYVDGWDXBHV-UHFFFAOYSA-N 0.000 title abstract 2
- 239000003112 inhibitor Substances 0.000 title abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000001153 fluoro group Chemical group F* 0.000 abstract 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- CTBSIWZADWNGPL-UHFFFAOYSA-N 1-(2-chlorophenyl)-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound N=1N=C2C(C)=NC3=CC=CC=C3N2C=1C1=CC=CC=C1Cl CTBSIWZADWNGPL-UHFFFAOYSA-N 0.000 abstract 1
- DGTJUXLZPAKEDG-UHFFFAOYSA-N 1-(2-methoxyphenyl)-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound COC1=CC=CC=C1C1=NN=C2N1C1=CC=CC=C1N=C2C DGTJUXLZPAKEDG-UHFFFAOYSA-N 0.000 abstract 1
- FDXFIVYCNRJKCU-UHFFFAOYSA-N 2-(4-methyl-[1,2,4]triazolo[4,3-a]quinoxalin-1-yl)phenol Chemical compound N=1N=C2C(C)=NC3=CC=CC=C3N2C=1C1=CC=CC=C1O FDXFIVYCNRJKCU-UHFFFAOYSA-N 0.000 abstract 1
- PKFKCXQPEAGAHL-UHFFFAOYSA-N 2-methoxy-6-(4-methyl-[1,2,4]triazolo[4,3-a]quinoxalin-1-yl)phenol Chemical compound COC1=CC=CC(C=2N3C4=CC=CC=C4N=C(C)C3=NN=2)=C1O PKFKCXQPEAGAHL-UHFFFAOYSA-N 0.000 abstract 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
- PDPJEMXSHLGRFT-UHFFFAOYSA-N 4-chloro-3-(4-methyl-[1,2,4]triazolo[4,3-a]quinoxalin-1-yl)aniline Chemical compound N=1N=C2C(C)=NC3=CC=CC=C3N2C=1C1=CC(N)=CC=C1Cl PDPJEMXSHLGRFT-UHFFFAOYSA-N 0.000 abstract 1
- KXSGJAHZGIIUIR-UHFFFAOYSA-N 4-methoxy-3-(4-methyl-[1,2,4]triazolo[4,3-a]quinoxalin-1-yl)aniline Chemical compound COC1=CC=C(N)C=C1C1=NN=C2N1C1=CC=CC=C1N=C2C KXSGJAHZGIIUIR-UHFFFAOYSA-N 0.000 abstract 1
- QKWYLCALFFTEAL-UHFFFAOYSA-N 4-methyl-1-(2-nitrophenyl)-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound N=1N=C2C(C)=NC3=CC=CC=C3N2C=1C1=CC=CC=C1[N+]([O-])=O QKWYLCALFFTEAL-UHFFFAOYSA-N 0.000 abstract 1
- WULGHPGREVSKPP-UHFFFAOYSA-N 4-methyl-3-(4-methyl-[1,2,4]triazolo[4,3-a]quinoxalin-1-yl)aniline Chemical compound CC1=CC=C(N)C=C1C1=NN=C2N1C1=CC=CC=C1N=C2C WULGHPGREVSKPP-UHFFFAOYSA-N 0.000 abstract 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 abstract 1
- 101001098814 Dictyostelium discoideum 3',5'-cyclic-nucleotide phosphodiesterase regA Proteins 0.000 abstract 1
- 210000003169 central nervous system Anatomy 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- -1 e.g. Chemical group 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
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- 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
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- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
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- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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Abstract
La presente se refiere a derivados de (1,2,4)triazolo[4,3-a]quinoxalina que son inhibidores de fosfodiesterasa 2 y/o 10, útiles en el tratamiento de enfermedades del sistema nervioso central.Reivindicación 1: Un compuesto de fórmula (1) o una de sus sales aceptables desde el punto de vista farmacéutico; en donde: R1 representa -fenilo, 2-piridilo, 3-piridilo o 4-piridilo, en cada caso sustituido con un sustituyente diferente de H en una posición orto de la ligadura a la estructura de la cadena principal y en forma opcional sustituido con sustituyentes adicionales diferentes de H; R2 representa hidrógeno, alquilo C1-4, en forma opcional sustituido con hasta 2 halo, por ej., átomos de flúor; R3, R4, R5 y R6 representan, en forma independiente unos de otros hidrógeno, halógeno, alquilo C1-4, en forma opcional sustituido con hasta 5, con preferencia hasta 3 halo, por ej., átomos de flúor, y/o -O(halo)alquilo C1-2, cicloalquilo C3-8, en forma opcional sustituido con halo, -haloalquilo C1-2 y/o O(halo)alquilo C1-2, CN, OH, -O-alquilo C1-4, en forma opcional sustituido con hasta 5, con preferencia hasta 3 halo, por ej., átomos de flúor, y/o -O(halo)alquilo C1-2, cicloalquilo C3-8 en forma opcional sustituido con halo, -haloalquilo C1-2 y/o -O(halo)alquilo C1-2, -O(CH2)n-R10, en donde n puede ser 1 ó 2; R10 representa: un grupo cíclico que puede ser no sustituido o sustituido con preferencia hasta 4 veces por halógeno, alquilo C1-4, en forma opcional sustituido con hasta 5, con preferencia hasta 3 átomos de halógeno, u O-alquilo C1-4, en forma opcional sustituido con hasta 5, con preferencia hasta 3 átomos de halógeno, pero no los siguientes compuestos: 1-(2-hidroxifenil)-4-metil-(1,2,4)triazolo[4,3-a]quinoxalina, 1-(2-clorofenil)-4-metil-(1,2,4)triazolo[4,3-a]quinoxalina, 1-(2-nitrofenil)-4-metil-(1,2,4)triazolo[4,3-a]quinoxalina, 1-(2-metoxifenil)-4-metil-(1,2,4)triazolo[4,3-a]quinoxalina, 1-(5-amino-2-clorofenil)-4-metil-(1,2,4)triazolo[4,3-a]quinoxalina, 1-(5-amino-2-metoxifenil)-4-metil(1,2,4)triazolo[4,3-a]quinoxalina, 1-(5-amino-2-metilfenil)-4-metil-(1,2,4)triazolo[4, 3-a]quinoxalina, o 1-(2-hidroxi-3-metoxifenil)-4-metil-(1,2,4)triazolo[4,3-a]quinoxalina.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161437848P | 2011-01-31 | 2011-01-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR085099A1 true AR085099A1 (es) | 2013-09-11 |
Family
ID=45833359
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP120100303A AR085099A1 (es) | 2011-01-31 | 2012-01-31 | Derivados de (1,2,4)triazolo[4,3-a]quinoxalina como inhibidores de fosfodiesterasas |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US9540379B2 (es) |
| EP (1) | EP2670754B1 (es) |
| JP (1) | JP6027547B2 (es) |
| KR (1) | KR20140019342A (es) |
| CN (1) | CN103459395A (es) |
| AR (1) | AR085099A1 (es) |
| AU (1) | AU2012213471B2 (es) |
| BR (1) | BR112013019354A2 (es) |
| CA (1) | CA2824929A1 (es) |
| CL (1) | CL2013002003A1 (es) |
| CO (1) | CO6811848A2 (es) |
| EA (1) | EA023792B1 (es) |
| EC (1) | ECSP13012824A (es) |
| GE (1) | GEP20156333B (es) |
| IL (1) | IL226826A (es) |
| MA (1) | MA34844B1 (es) |
| MX (1) | MX2013008667A (es) |
| PE (1) | PE20141023A1 (es) |
| PH (1) | PH12013501355A1 (es) |
| SG (1) | SG192210A1 (es) |
| TN (1) | TN2013000325A1 (es) |
| TW (1) | TWI535718B (es) |
| UA (1) | UA111963C2 (es) |
| UY (1) | UY33888A (es) |
| WO (1) | WO2012104293A1 (es) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10604523B2 (en) * | 2011-06-27 | 2020-03-31 | Janssen Pharmaceutica Nv | 1-aryl-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline derivatives |
| WO2013034758A1 (en) * | 2011-09-09 | 2013-03-14 | H. Lundbeck A/S | Substituted triazolopyrazines and uses thereof |
| JP2014526453A (ja) * | 2011-09-09 | 2014-10-06 | ハー・ルンドベック・アクチエゼルスカベット | ピリジン化合物およびそれらの使用 |
| WO2013034755A1 (en) * | 2011-09-09 | 2013-03-14 | H. Lundbeck A/S | Triazolopyrazine derivatives and their use for treating neurological and psychiatric disorders |
| JP6426603B2 (ja) | 2012-06-26 | 2018-11-21 | ヤンセン ファーマシューティカ エヌ．ベー． | 神経障害または代謝障害の治療に使用するための、１−アリール−４−メチル−［１，２，４］トリアゾロ［４，３−ａ］−キノキサリン化合物などのＰＤＥ２阻害剤とＰＤＥ１０阻害剤との組合せ |
| US20140045856A1 (en) | 2012-07-31 | 2014-02-13 | Boehringer Ingelheim International Gmbh | 4-Methyl-2,3,5,9,9b-pentaaza-cyclopenta[a]naphthalenes |
| WO2014139983A1 (en) | 2013-03-13 | 2014-09-18 | H. Lundbeck A/S | [1,2,4]triazolo[4,3-a]quinoxalines as dual pde2/pde10 inhibitors |
| EP3091983B1 (en) | 2014-01-08 | 2019-10-02 | Intra-Cellular Therapies, Inc. | Pharmaceutical compositions comprising a pde-1 inhibitor and a pde-2 inhibitor |
| CN106459062A (zh) | 2014-04-23 | 2017-02-22 | 达特神经科学(开曼)有限公司 | 作为PDE2抑制剂的取代的[1,2,4]三唑并[1,5‑a]嘧啶‑7‑基化合物 |
| TWI568737B (zh) | 2014-11-05 | 2017-02-01 | 達特神經科學（開曼）有限責任公司 | 作為ｐｄｅ２抑制劑之經取代的５－甲基－［１，２，４］三唑并［１，５－ａ］嘧啶－２－胺化合物 |
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| TN2013000325A1 (en) | 2015-01-20 |
| CO6811848A2 (es) | 2013-12-16 |
| TW201245198A (en) | 2012-11-16 |
| JP6027547B2 (ja) | 2016-11-16 |
| CN103459395A (zh) | 2013-12-18 |
| EP2670754A1 (en) | 2013-12-11 |
| EP2670754B1 (en) | 2017-05-24 |
| AU2012213471A1 (en) | 2013-07-04 |
| US20120302564A1 (en) | 2012-11-29 |
| PH12013501355A1 (en) | 2013-09-02 |
| PE20141023A1 (es) | 2014-09-04 |
| EA023792B1 (ru) | 2016-07-29 |
| CL2013002003A1 (es) | 2013-12-06 |
| NZ611630A (en) | 2015-03-27 |
| UA111963C2 (uk) | 2016-07-11 |
| UY33888A (es) | 2012-08-31 |
| SG192210A1 (en) | 2013-09-30 |
| MX2013008667A (es) | 2013-10-01 |
| IL226826A (en) | 2016-10-31 |
| GEP20156333B (en) | 2015-07-27 |
| KR20140019342A (ko) | 2014-02-14 |
| CA2824929A1 (en) | 2012-08-09 |
| AU2012213471B2 (en) | 2016-07-14 |
| ECSP13012824A (es) | 2013-10-31 |
| BR112013019354A2 (pt) | 2019-09-24 |
| EA201300871A1 (ru) | 2014-01-30 |
| WO2012104293A1 (en) | 2012-08-09 |
| US9540379B2 (en) | 2017-01-10 |
| TWI535718B (zh) | 2016-06-01 |
| JP2014503576A (ja) | 2014-02-13 |
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