AR105179A1 - Derivados de piridina o pirimidina como inhibidores de cdk9 - Google Patents
Derivados de piridina o pirimidina como inhibidores de cdk9Info
- Publication number
- AR105179A1 AR105179A1 ARP160101956A ARP160101956A AR105179A1 AR 105179 A1 AR105179 A1 AR 105179A1 AR P160101956 A ARP160101956 A AR P160101956A AR P160101956 A ARP160101956 A AR P160101956A AR 105179 A1 AR105179 A1 AR 105179A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- ring
- nhc
- nr10c
- cycloalkyl
- Prior art date
Links
Classifications
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- 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
- C07D498/04—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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Abstract
Se provee una serie de derivados de piridina o pirimidina que inhiben CDK9 y pueden ser útiles para el tratamiento de enfermedades hiperproliferativas. En particular, los compuestos son útiles en el tratamiento de enfermedades proliferativas como por ejemplo cáncer, incluyendo trastornos hematológicos malignos, como por ejemplo leucemia mieloide aguda, mieloma múltiple, leucemia linfocítica crónica, linfoma difuso de células B grandes, linfoma de Burkitt, linfoma folicular y tumores sólidos como por ejemplo cáncer de mama, cáncer de pulmón, neuroblastoma y cáncer de colon. Reivindicación 1: Un compuesto caracterizado porque es de fórmula (1) donde: A es C(R⁵) o N; R⁵ es H, C₁₋₃ alquilo, CN o halógeno; R² es heterocicloalquilo de 3 - 7 miembros o cicloalquilo de 3 - 7 miembros; opcionalmente sustituido con entre uno y tres sustituyentes seleccionados en forma independiente entre el grupo que consiste en R¹⁰, OR¹⁰, SR¹⁰, S(O)R¹⁰, S(O)₂R¹⁰, C(O)R¹⁰, C(O)OR¹⁰, OC(O)R¹⁰, OC(O)OR¹⁰, NH₂, NHR¹⁰, N(R¹⁰)₂, NHC(O)H, NHC(O)R¹⁰, NR¹⁰C(O)H, NR¹⁰C(O)R¹⁰, NHS(O)₂R¹⁰, NR¹⁰S(O)₂R¹⁰, NHC(O)OR¹⁰, NR¹⁰C(O)OR¹⁰, NHC(O)NH₂, NHC(O)NHR¹⁰, NHC(O)N(R¹⁰)₂, NR¹⁰C(O)NH₂, NR¹⁰C(O)NHR¹⁰, NR¹⁰C(O)N(R¹⁰)₂, C(O)NH₂, C(O)NHR¹⁰, C(O)N(R¹⁰)₂, C(O)NHOH, C(O)NHOR¹⁰, C(O)NHS(O)₂R¹⁰, C(O)NR¹⁰S(O)₂R¹⁰, S(O)₂NH₂, S(O)₂NHR¹⁰, S(O)₂N(R¹⁰)₂, S(O)₂NHC(O)OR¹⁰, S(O)₂NR¹⁰C(O)OR¹⁰, C(O)H, C(O)OH, OH, CN, NO₂, F, Cl, Br y I; donde uno o más grupos CH₂ del anillo pueden reemplazarse opcionalmente por la cantidad correspondiente de grupos -C(O), uno o más átomos de azufre o nitrógeno del anillo opcionalmente pueden estar oxidados formando S-óxidos o N-óxidos; R¹⁰, en cada caso, se selecciona en forma independiente entre el grupo que consiste en un grupo cicloalquilo o heterocicloalquilo de entre 3 y 6 miembros, C₁₋₆ alquilo, -O-C₁₋₆ alquilo, C₁₋₆ alquil-O-C₁₋₆ alquilo, NH₂, C(O)NH₂, C(O)H, C(O)OH, OH, CN, NO₂, F, Cl, Br y I; donde dos grupos R¹⁰ junto con los átomos a los cuales están unidos pueden formar un grupo cicloalquilo o heterocicloalquilo de entre 3 y 6 miembros; y cada grupo R¹⁰ alquilo, cicloalquilo y heterocicloalquilo mencionado precedentemente puede estar sustituido adicionalmente con uno o dos sustituyentes seleccionados en forma independiente entre CN, OH, halógeno, C₁₋₃ alquilo, -O-C₁₋₃ alquilo, NH₂, NH-C₁₋₃ alquilo, y NHC(O)-C₁₋₃ alquilo; R⁴ es un resto de fórmula (2) ó (3) donde X e Y junto con los átomos a los cuales están unidos, forman un anillo heterocicloalquilo de entre 5 y 7 miembros que, además del nitrógeno puente, puede contener uno o dos heteroátomos seleccionados entre N, O, y S, donde el anillo puede ser saturado o parcialmente saturado; donde uno o dos grupos CH₂ del anillo pueden reemplazarse opcionalmente por la cantidad correspondiente de grupos -C(O), uno o más átomos de azufre o nitrógeno del anillo opcionalmente pueden estar oxidados formando S-óxidos o N-óxidos y donde el anillo puede estar sustituido sobre un carbono del anillo con uno o dos sustituyentes R¹⁰ o sobre un nitrógeno del anillo con un sustituyente R¹²; J es N o CR¹¹; y R¹¹ es H, C₁₋₃ alquilo; R¹² se selecciona en cada caso en forma independiente entre el grupo que consiste en un grupo cicloalquilo o heterocicloalquilo de entre 3 y 6 miembros, C₁₋₆ alquilo, C₁₋₆ alquil-O-C₁₋₆ alquilo, C(O)NH₂, C(O)H; donde el grupo R¹² alquilo, cicloalquilo y heterocicloalquilo puede estar sustituido adicionalmente con uno o dos sustituyentes seleccionados en forma independiente entre CN, OH, y halógeno, C₁₋₃ alquilo, NH₂, y NH-C₁₋₃ alquilo, NHC(O)-C₁₋₃ alquilo; o sales farmacéuticamente aceptables de los mismos.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562185852P | 2015-06-29 | 2015-06-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR105179A1 true AR105179A1 (es) | 2017-09-13 |
Family
ID=56292699
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP160101956A AR105179A1 (es) | 2015-06-29 | 2016-06-28 | Derivados de piridina o pirimidina como inhibidores de cdk9 |
Country Status (35)
| Country | Link |
|---|---|
| US (4) | US9845331B2 (es) |
| EP (2) | EP3539961B1 (es) |
| JP (1) | JP6997627B2 (es) |
| CN (1) | CN107873028B (es) |
| AR (1) | AR105179A1 (es) |
| AU (1) | AU2016286200B2 (es) |
| BR (1) | BR122019013677B1 (es) |
| CA (1) | CA2989499C (es) |
| CL (1) | CL2017003306A1 (es) |
| CO (1) | CO2017013713A2 (es) |
| CR (2) | CR20210297A (es) |
| CY (2) | CY1122111T1 (es) |
| DK (2) | DK3313838T3 (es) |
| DO (2) | DOP2017000295A (es) |
| EA (1) | EA035383B1 (es) |
| ES (2) | ES2902148T3 (es) |
| HR (2) | HRP20211970T1 (es) |
| HU (2) | HUE043440T2 (es) |
| IL (1) | IL256393B (es) |
| LT (2) | LT3539961T (es) |
| ME (1) | ME03404B (es) |
| MX (1) | MX371034B (es) |
| NI (1) | NI201700174A (es) |
| PE (1) | PE20180530A1 (es) |
| PH (1) | PH12017502334A1 (es) |
| PL (2) | PL3539961T3 (es) |
| PT (2) | PT3313838T (es) |
| RS (2) | RS62781B1 (es) |
| SI (2) | SI3539961T1 (es) |
| SV (1) | SV2017005598A (es) |
| TN (1) | TN2017000486A1 (es) |
| TR (1) | TR201909286T4 (es) |
| TW (1) | TWI723028B (es) |
| WO (1) | WO2017001354A1 (es) |
| ZA (1) | ZA201800563B (es) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2018335617B2 (en) | 2017-09-25 | 2021-12-09 | Astrazeneca Ab | Combination of a BTK inhibitor and an inhibitor of CDK9 to treat cancer |
| EP3694506B1 (en) * | 2017-10-09 | 2023-08-02 | Merck Sharp & Dohme LLC | Novel substituted phenyloxetane and phenyltetrahydrofuran compounds as indoleamine 2,3-dioxygenase (ido) inhibitors |
| CN108129288B (zh) * | 2017-12-27 | 2021-01-22 | 上海毕得医药科技股份有限公司 | 一种反式-3-羟基环丁基甲酸的合成方法 |
| TW202344250A (zh) | 2018-11-14 | 2023-11-16 | 瑞典商阿斯特捷利康公司 | 治療癌症之方法 |
| CA3153531A1 (en) * | 2019-09-11 | 2021-03-18 | Prelude Therapeutics Incorporated | Cdk inhibitors and their use as pharmaceuticals |
| JP7406008B2 (ja) * | 2020-05-12 | 2023-12-26 | 蘇州阿尓脈生物科技有限公司 | Ｃｄｋ９阻害剤としての多環式アミド系誘導体、その調製方法及び用途 |
| WO2021227906A1 (zh) | 2020-05-12 | 2021-11-18 | 苏州阿尔脉生物科技有限公司 | 一种作为cdk抑制剂的吡啶乙酰胺类衍生物、其制备方法及用途 |
| TW202216207A (zh) | 2020-06-24 | 2022-05-01 | 英商阿斯特捷利康英國股份有限公司 | 抗體-藥物結合物及cdk9抑制劑之組合 |
| WO2022028556A1 (zh) | 2020-08-07 | 2022-02-10 | 南京药石科技股份有限公司 | Cdk9抑制剂及其用途 |
| TWI809330B (zh) * | 2020-11-20 | 2023-07-21 | 大陸商勁方醫藥科技(上海)有限公司 | Cdk9抑制劑的多晶型物及其製法和用途 |
| CN115381824A (zh) * | 2021-05-24 | 2022-11-25 | 石药集团中奇制药技术（石家庄）有限公司 | 周期蛋白依赖性激酶9抑制剂的用途 |
| CN115381823A (zh) * | 2021-05-24 | 2022-11-25 | 石药集团中奇制药技术（石家庄）有限公司 | 一种周期蛋白依赖性激酶9抑制剂的用途 |
| CN117813289A (zh) * | 2021-07-14 | 2024-04-02 | 上海海雁医药科技有限公司 | 吡唑衍生物及其中间体和制备方法 |
| US20230279016A1 (en) * | 2021-12-23 | 2023-09-07 | The Katholieke Universiteit Leuven | Tetrahydropyrazolopyrimidines and Related Analogs for Inhibiting YAP/TAZ-TEAD |
| WO2024039210A1 (ko) | 2022-08-17 | 2024-02-22 | 한국화학연구원 | Cdk2 및/또는 cdk9의 억제 또는 분해용 화합물 및 이들의 의약 용도 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008133192A1 (ja) | 2007-04-19 | 2008-11-06 | Takeda Pharmaceutical Company Limited | 縮合イミダゾール化合物およびその用途 |
| US8389521B2 (en) | 2007-04-24 | 2013-03-05 | Ingenium Pharmaceuticals Gmbh | Inhibitors of protein kinases |
| JP5566880B2 (ja) | 2007-04-24 | 2014-08-06 | インゲニウム ファーマシューティカルズ ジーエムビーエイチ | プロテインキナーゼの阻害剤としての４，６−二置換アミノピリミジン誘導体 |
| JP5379787B2 (ja) | 2007-04-24 | 2013-12-25 | インゲニウム ファーマシューティカルズ ジーエムビーエイチ | プロテインキナーゼの阻害剤 |
| ES2539518T3 (es) | 2007-04-24 | 2015-07-01 | Astrazeneca Ab | Inhibidores de proteínas quinasas |
| WO2008132138A1 (en) | 2007-04-25 | 2008-11-06 | Ingenium Pharmaceuticals Gmbh | Derivatives of 4,6-disubstituted aminopyrimidines |
| EP2212297B1 (en) | 2007-10-12 | 2011-05-25 | Ingenium Pharmaceuticals GmbH | Inhibitors of protein kinases |
| US20120157433A1 (en) | 2009-09-04 | 2012-06-21 | Pfister Keith B | Heteroaryl Compounds as Kinase Inhibitors |
| US20110113038A1 (en) | 2009-11-12 | 2011-05-12 | International Business Machines Corporation | Search term security |
| GB201002911D0 (en) | 2010-02-19 | 2010-04-07 | Medical Res Council | Compound |
| AU2011226073B2 (en) | 2010-03-10 | 2015-05-28 | Astrazeneca Ab | 4-Phenyl pyridine analogues as protein kinase inhibitors. |
| AR081810A1 (es) | 2010-04-07 | 2012-10-24 | Bayer Cropscience Ag | Piridinilpirazoles biciclicos |
| WO2012066065A1 (en) | 2010-11-17 | 2012-05-24 | Novartis Ag | Phenyl-heteroaryl amine compounds and their uses |
| WO2012101063A1 (en) | 2011-01-28 | 2012-08-02 | Novartis Ag | N-acyl pyridine biaryl compounds and their uses |
| WO2012101064A1 (en) * | 2011-01-28 | 2012-08-02 | Novartis Ag | N-acyl pyrimidine biaryl compounds as protein kinase inhibitors |
| EP2668162A1 (en) * | 2011-01-28 | 2013-12-04 | Novartis AG | Substituted bi-heteroaryl compounds as cdk9 inhibitors and their uses |
| KR20140072177A (ko) | 2011-10-06 | 2014-06-12 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | 헤테로사이클릴피리(미)디닐피라졸 |
| CN105026393A (zh) | 2013-03-13 | 2015-11-04 | 艾伯维公司 | Cdk9激酶抑制剂 |
| JP2016516710A (ja) | 2013-03-13 | 2016-06-09 | アッヴィ・インコーポレイテッド | ピリジン系ｃｄｋ９キナーゼ阻害薬 |
| WO2014160028A1 (en) | 2013-03-14 | 2014-10-02 | Abbvie Inc. | Pyrrolopyrimindine cdk9 kinase inhibitors |
| TW201446763A (zh) | 2013-03-14 | 2014-12-16 | Abbvie Inc | 吡咯并［２，３－ｂ］吡啶ｃｄｋ９激酶抑制劑 |
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2016
- 2016-06-27 DK DK16733459.8T patent/DK3313838T3/da active
- 2016-06-27 ES ES19165726T patent/ES2902148T3/es active Active
- 2016-06-27 BR BR122019013677-7A patent/BR122019013677B1/pt active IP Right Grant
- 2016-06-27 CN CN201680029447.9A patent/CN107873028B/zh active Active
- 2016-06-27 PT PT16733459T patent/PT3313838T/pt unknown
- 2016-06-27 TR TR2019/09286T patent/TR201909286T4/tr unknown
- 2016-06-27 PT PT191657261T patent/PT3539961T/pt unknown
- 2016-06-27 HU HUE16733459A patent/HUE043440T2/hu unknown
- 2016-06-27 TN TNP/2017/000486A patent/TN2017000486A1/en unknown
- 2016-06-27 RS RS20220005A patent/RS62781B1/sr unknown
- 2016-06-27 CR CR20210297A patent/CR20210297A/es unknown
- 2016-06-27 ES ES16733459T patent/ES2728356T3/es active Active
- 2016-06-27 WO PCT/EP2016/064899 patent/WO2017001354A1/en active Application Filing
- 2016-06-27 EP EP19165726.1A patent/EP3539961B1/en active Active
- 2016-06-27 HR HRP20211970TT patent/HRP20211970T1/hr unknown
- 2016-06-27 PL PL19165726T patent/PL3539961T3/pl unknown
- 2016-06-27 AU AU2016286200A patent/AU2016286200B2/en active Active
- 2016-06-27 PL PL16733459T patent/PL3313838T3/pl unknown
- 2016-06-27 EP EP16733459.8A patent/EP3313838B1/en active Active
- 2016-06-27 CA CA2989499A patent/CA2989499C/en active Active
- 2016-06-27 SI SI201631427T patent/SI3539961T1/sl unknown
- 2016-06-27 LT LTEP19165726.1T patent/LT3539961T/lt unknown
- 2016-06-27 SI SI201630247T patent/SI3313838T1/sl unknown
- 2016-06-27 RS RS20190564A patent/RS58712B1/sr unknown
- 2016-06-27 DK DK19165726.1T patent/DK3539961T3/da active
- 2016-06-27 US US15/193,826 patent/US9845331B2/en active Active
- 2016-06-27 CR CR20170596A patent/CR20170596A/es unknown
- 2016-06-27 JP JP2017567737A patent/JP6997627B2/ja active Active
- 2016-06-27 LT LTEP16733459.8T patent/LT3313838T/lt unknown
- 2016-06-27 PE PE2017002874A patent/PE20180530A1/es unknown
- 2016-06-27 MX MX2017016244A patent/MX371034B/es active IP Right Grant
- 2016-06-27 EA EA201890094A patent/EA035383B1/ru not_active IP Right Cessation
- 2016-06-27 ME MEP-2019-138A patent/ME03404B/me unknown
- 2016-06-27 HU HUE19165726A patent/HUE057343T2/hu unknown
- 2016-06-28 AR ARP160101956A patent/AR105179A1/es unknown
- 2016-06-28 TW TW105120362A patent/TWI723028B/zh active
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2017
- 2017-12-06 US US15/833,277 patent/US10717746B2/en active Active
- 2017-12-12 DO DO2017000295A patent/DOP2017000295A/es unknown
- 2017-12-15 PH PH12017502334A patent/PH12017502334A1/en unknown
- 2017-12-18 IL IL256393A patent/IL256393B/en unknown
- 2017-12-20 SV SV2017005598A patent/SV2017005598A/es unknown
- 2017-12-21 CL CL2017003306A patent/CL2017003306A1/es unknown
- 2017-12-22 NI NI201700174A patent/NI201700174A/es unknown
- 2017-12-28 CO CONC2017/0013713A patent/CO2017013713A2/es unknown
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2018
- 2018-01-26 ZA ZA2018/00563A patent/ZA201800563B/en unknown
- 2018-09-25 DO DO2018000207A patent/DOP2018000207A/es unknown
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2019
- 2019-04-19 HR HRP20190748TT patent/HRP20190748T1/hr unknown
- 2019-06-19 CY CY20191100636T patent/CY1122111T1/el unknown
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2020
- 2020-07-17 US US16/931,786 patent/US11352369B2/en active Active
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2021
- 2021-12-22 CY CY20211101125T patent/CY1125066T1/el unknown
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2022
- 2022-04-27 US US17/660,935 patent/US20220340592A1/en active Pending
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