AR096727A1 - Derivados terapéuticamente activos de estratrien-tiazol - Google Patents
Derivados terapéuticamente activos de estratrien-tiazolInfo
- Publication number
- AR096727A1 AR096727A1 ARP140102397A ARP140102397A AR096727A1 AR 096727 A1 AR096727 A1 AR 096727A1 AR P140102397 A ARP140102397 A AR P140102397A AR P140102397 A ARP140102397 A AR P140102397A AR 096727 A1 AR096727 A1 AR 096727A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- group
- perhaloalkyl
- haloalkyl
- independently selected
- Prior art date
Links
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 7
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 3
- 125000005842 heteroatom Chemical group 0.000 abstract 3
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- 230000001419 dependent effect Effects 0.000 abstract 2
- 208000035475 disorder Diseases 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 239000003270 steroid hormone Substances 0.000 abstract 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 abstract 1
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 abstract 1
- 101100439664 Arabidopsis thaliana CHR8 gene Proteins 0.000 abstract 1
- 102000004190 Enzymes Human genes 0.000 abstract 1
- 108090000790 Enzymes Proteins 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 230000006806 disease prevention Effects 0.000 abstract 1
- 229960005309 estradiol Drugs 0.000 abstract 1
- 229930182833 estradiol Natural products 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 230000005764 inhibitory process Effects 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- -1 perhaloalkyl C1−3 Chemical group 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000002730 succinyl group Chemical group C(CCC(=O)*)(=O)* 0.000 abstract 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/12—Ophthalmic agents for cataracts
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/28—Antiandrogens
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/32—Antioestrogens
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J51/00—Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (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)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Ophthalmology & Optometry (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Obesity (AREA)
- Dermatology (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Neurosurgery (AREA)
- Child & Adolescent Psychology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Abstract
Su uso como inhibidores de 17b-HSD1 y el tratamiento o la prevención de enfermedades o trastornos dependientes de la hormona esteroide, tales como enfermedades o trastornos dependientes de la hormona esteroide que requieren la inhibición de la enzima 17b-HSD1 y/o requieren la disminución de la concentración endógena de estradiol. Además se relaciona con la preparación de los compuestos mencionados y con composiciones farmacéuticas que comprenden como ingrediente(s) activo(s) uno o varios de los compuestos mencionados o sus sales farmacéuticamente aceptables. Reivindicación 1: Un compuesto de la fórmula (1) donde (i-a) R² y R⁴ se seleccionan cada uno independientemente del grupo que consiste en H, halógeno, alquilo C₁₋₆, haloalquilo C₁₋₃, perhaloalquilo C₁₋₃, CN, NO₂, N₃, N(R)₂, (CH₂)ₙN(R)₂, OR, (CH₂)ₙOR, CO₂R, CONHR, NHCOR, SCOR o COR; y R³ se selecciona del grupo que consiste en H, alquilo C₁₋₆, haloalquilo C₁₋₃, perhaloalquilo C₁₋₃, N(R)₂. N₃ y OR³, donde R³ se selecciona del grupo que consiste en R, bencilo, succinilo, glucuronilo opcionalmente acilado, anillo heterocíclico saturado de 5 a 6 miembros que comprende 1 ó 2 heteroátomos independientemente seleccionados de N y O, (CH₂)ₙOH, SO₂OH, SO₂R, tosilo, SO₂N(R)₂, PO(OR)₂, C(O)N(R)₂, C(O)(CH₂)ₙN(R)₂, y C(O)R; o (i-b) R² y R³ o R³ y R⁴, conjuntamente con los átomos de carbono en el anillo al cual están unidos, forman un anillo heterocíclico insaturado o aromático de 5 miembros que comprende 1 ó 2 heteroátomos cada uno independientemente seleccionado de N y O, opcionalmente sustituido con metilo u oxo; y R⁴ o R², respectivamente, es H y; (ii-a) uno de R⁷ y R⁸ es OR⁷, donde R⁷ se selecciona del grupo que consiste en H o alquilo C₁₋₆ y el otro se selecciona del grupo que consiste en H, alquilo C₁₋₆, haloalquilo C₁₋₃, perhaloalquilo C₁₋₃, alquenilo C₂₋₆, alquinilo C₂₋₆, bencilo, (CH₂)ₙCN, (CH₂)ₙOH, N(R)₂, (CH₂)ₙN(R)₂, C(O)OR, (CH₂)ₙC(O)OR, C(O)N(R)₂, (CH₂)ₙC(O)NH₂, OR⁷, COR, NHCO-alquilo C₁₋₆, -COCH₂O-P(O)(OH)₂; o (ii-b) uno de R⁷ y R⁸ es H y el otro se selecciona del grupo que consiste en halógeno, haloalquilo C₁₋₃, perhaloalquilo C₁₋₃, (CH₂)ₙCN, OSO₂OH, OSO₂R, O-tosilo, OC(O)R, OC(O)(CH₂)ₙCOOR, OC(O)(CH₂)ₙN(R)₂, OC(O)CH₂NHC(O)OR, OPO(OR)₂, N₃, N(R)₂, NH(CH₂)ₘOR, NH(CH₂)ₘSR, NH(CH₂)ₘNR₂, NHOR y NHC(O)R; o (ii-c) R⁷ y R⁸ forman juntos un grupo seleccionado del grupo que consiste en =CH₂, =CHR⁸ y CHCOOR⁷, donde R⁸ es alquilo C₁₋₆, alcoxi C₁₋₆ o fenilo; R es H o alquilo C₁₋₆, haloalquilo C₁₋₃, o perhaloalquilo C₁₋₃, o cuando una parte de cualquiera de N(R)₂ ambos R junto con el nitrógeno al que están unidos pueden formar un anillo heterocíclico alifático o aromático de 5 a 6 miembros que comprende 1 ó 2 heteroátomos cada uno independientemente seleccionado de N y O; R es alquilo C₁₋₆, haloalquilo C₁₋₃, o perhaloalquilo C₁₋₃; R es alquilo C₁₋₁₈, alquenilo C₂₋₁₈, -(CH₂)ₙ-cicloalquilo C₃₋₆, o fenilo opcionalmente sustituido; y n es 0 1 ó 2; m es 1, 2 ó 3; o una sal farmacéuticamente aceptable de este.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI20135695 | 2013-06-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR096727A1 true AR096727A1 (es) | 2016-01-27 |
Family
ID=51220585
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP140102397A AR096727A1 (es) | 2013-06-25 | 2014-06-25 | Derivados terapéuticamente activos de estratrien-tiazol |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US9850272B2 (es) |
| EP (1) | EP3013847B1 (es) |
| JP (1) | JP6456373B2 (es) |
| CN (1) | CN105518017B (es) |
| AR (1) | AR096727A1 (es) |
| TW (1) | TW201522359A (es) |
| WO (1) | WO2014207311A1 (es) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3237431B1 (en) | 2014-12-23 | 2019-03-20 | Forendo Pharma Ltd | Prodrugs of 17.beta.-hsd1 -inhibitors |
| CZ307437B6 (cs) | 2016-06-07 | 2018-08-22 | Ăšstav organickĂ© chemie a biochemie AV ÄŚR, v.v.i. | 15β-substituované deriváty estronu jako selektivní inhibitory 17β-hydroxysteoiddehydrogenáz |
| DK3634975T3 (da) | 2017-06-08 | 2024-05-27 | Organon R&D Finland Ltd | 17-oximer af 15.beta.-[3-propanamido]-substituerede estra-1,3,5(10)-trien-17-oner til anvendelse i inhibition af 17.beta.-hydroxysteroid-dehydrogenaser |
| EP3891167B1 (en) | 2018-12-05 | 2024-11-13 | Organon R&D Finland Oy | Estra-1,3,5(10)-triene compounds condensed in position 16(17) with a pyrazole ring as inhibitors of 17-hsd1 |
| CN114644673B (zh) * | 2020-12-19 | 2023-12-26 | 上海喀露蓝科技有限公司 | 一种雌二醇衍生物、其制备方法及其在医药上的用途 |
| AR133544A1 (es) * | 2023-08-15 | 2025-10-08 | Univ Laval | INHIBIDORES IRREVERSIBLES DE 17b-HSD1 |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2323089A1 (en) | 1998-03-11 | 1999-09-16 | Endorecherche, Inc. | Inhibitors of type 5 and type 3 17.beta.-hydroxysteroid dehydrogenase and methods for their use |
| DE69935335T2 (de) | 1998-08-07 | 2007-11-22 | Novartis Vaccines and Diagnostics, Inc., Emeryville | Pyrazole als modulatoren des östrogenrezeptors |
| GB9929302D0 (en) | 1999-12-11 | 2000-02-02 | Univ Cardiff | Benzyl tetralins compositions and uses thereof |
| AU2001288386B2 (en) * | 2000-11-27 | 2006-11-02 | Entremed, Inc. | 2-substituted estrogens as antiangiogenic agents |
| AR036492A1 (es) | 2001-09-06 | 2004-09-15 | Schering Corp | Inhibidores de la 17beta-hidroxiesteroide deshidrogenasa tipo 3, composiciones farmaceuticas y el uso de dichos inhibidores para la elaboracion de un medicamento para el tratamiento de enfermedades androgeno dependientes |
| ES2347643T3 (es) | 2001-10-17 | 2010-11-03 | Schering Corporation | Piperin- y piperazinacetamidas como inhibidores de 17beta hidroxiesteroide deshidrogenasa tipo 3 para el tratamiento de enfermedades dependientes de androgenos. |
| US6750248B2 (en) | 2001-11-09 | 2004-06-15 | National University Of Singapore | Methods for preparing an estrogenic preparation and isolated estrogenic compounds from a plant and uses thereof |
| JP4614770B2 (ja) | 2002-11-18 | 2011-01-19 | シェーリング コーポレイション | アンドロゲン依存性疾患を処置するための１７β−ヒドロキシステロイドデヒドロゲナーゼタイプ３インヒビター |
| AU2003293555A1 (en) | 2002-12-17 | 2004-07-29 | Schering Corporation | 17 beta-hydroxysteroid dehydrogenase type 3 inhibitors for the treatment of androgen dependent diseases |
| WO2004085345A2 (en) | 2003-03-21 | 2004-10-07 | Yale University | 15α-SUBSTITUTED ESTRADIOL CARBOXYLIC ACID ESTERS AS LOCALLY ACTIVE ESTROGENS |
| GB0306718D0 (en) | 2003-03-24 | 2003-04-30 | Sterix Ltd | Compound |
| US7465739B2 (en) | 2003-06-10 | 2008-12-16 | Solvay Pharmaceuticals B.V. | Compounds and their use in therapy |
| US7754709B2 (en) | 2003-06-10 | 2010-07-13 | Solvay Pharmaceuticals Bv | Tetracyclic thiophenepyrimidinone compounds as inhibitors of 17β hydroxysteroid dehydrogenase compounds |
| TWI331154B (en) | 2003-11-12 | 2010-10-01 | Solvay Pharm Gmbh | Novel 17-hydroxysteroid dehydrogenase type i inhibitors |
| US7378426B2 (en) | 2004-03-01 | 2008-05-27 | Bristol-Myers Squibb Company | Fused heterotricyclic compounds as inhibitors of 17β-hydroxysteroid dehydrogenase 3 |
| DE102004032673A1 (de) | 2004-07-02 | 2006-01-26 | Schering Ag | Neue 2-substituierte D-Homo-estra-1,3,5(10)-triene als Inhibitoren der 17ß-Hydroxysteroiddehydrogenase Typ 1 |
| DE102004032674A1 (de) | 2004-07-02 | 2006-01-26 | Schering Ag | Neue 2-substituierte Estra-1,3,5(10)-trien-17-one als Inhibitoren der 17β-Hydroxysteroiddehydrogenase Typ 1 |
| UA89964C2 (ru) | 2004-09-08 | 2010-03-25 | Н.В. Органон | 15β-ЗАМЕЩЕННЫЕ СТЕРОИДЫ, КОТОРЫЕ ИМЕЮТ СЕЛЕКТИВНУЮ ЭСТРОГЕННУЮ АКТИВНОСТЬ |
| ES2388297T3 (es) * | 2005-05-26 | 2012-10-11 | Abbott Products Gmbh | Inhibidores de 17-HSD1 y STS |
| US8030298B2 (en) * | 2005-05-26 | 2011-10-04 | Abbott Products Gmbh | 17β-HSD1 and STS inhibitors |
| WO2008034796A2 (en) | 2006-09-19 | 2008-03-27 | Solvay Pharmaceuticals Gmbh | Estratriene derivatives and their uses as 17beta-hydr0xyster0id dehydrogenase inhibitors |
| AU2007327653B2 (en) * | 2006-11-30 | 2013-04-18 | Solvay Pharmaceuticals Gmbh | Substituted estratrien derivatives as 17beta HSD inhibitors |
| US8288367B2 (en) * | 2006-11-30 | 2012-10-16 | Solvay Pharmaceuticals Gmbh | Substituted estratriene derivatives as 17BETA HSD inhibitors |
| JP2014508784A (ja) * | 2011-03-25 | 2014-04-10 | ユニヴェルシテ ラヴァル | １７β−ＨＳＤ１、１７β−ＨＳＤ３、および１７β−ＨＳＤ１０の阻害剤 |
-
2014
- 2014-06-25 AR ARP140102397A patent/AR096727A1/es unknown
- 2014-06-25 JP JP2016522680A patent/JP6456373B2/ja active Active
- 2014-06-25 US US14/392,290 patent/US9850272B2/en active Active
- 2014-06-25 TW TW103121872A patent/TW201522359A/zh unknown
- 2014-06-25 EP EP14742255.4A patent/EP3013847B1/en active Active
- 2014-06-25 CN CN201480046831.0A patent/CN105518017B/zh active Active
- 2014-06-25 WO PCT/FI2014/050519 patent/WO2014207311A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| US9850272B2 (en) | 2017-12-26 |
| JP2016527212A (ja) | 2016-09-08 |
| US20170081356A1 (en) | 2017-03-23 |
| WO2014207311A1 (en) | 2014-12-31 |
| EP3013847A1 (en) | 2016-05-04 |
| TW201522359A (zh) | 2015-06-16 |
| EP3013847B1 (en) | 2019-08-21 |
| CN105518017B (zh) | 2020-07-14 |
| JP6456373B2 (ja) | 2019-01-23 |
| CN105518017A (zh) | 2016-04-20 |
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