CN105102468A - 用于治疗hiv的c-3烷基和烯基修饰的桦木酸衍生物 - Google Patents
用于治疗hiv的c-3烷基和烯基修饰的桦木酸衍生物 Download PDFInfo
- Publication number
- CN105102468A CN105102468A CN201480010426.3A CN201480010426A CN105102468A CN 105102468 A CN105102468 A CN 105102468A CN 201480010426 A CN201480010426 A CN 201480010426A CN 105102468 A CN105102468 A CN 105102468A
- Authority
- CN
- China
- Prior art keywords
- alkyl
- substituted
- mmol
- cycloalkyl
- pentamethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 0 CC1CN(*)CCC1 Chemical compound CC1CN(*)CCC1 0.000 description 24
- VPFDJYDFKGJMOA-QAYJEQJRSA-N CC(C)(CCC(C(C)(C)[C@@H]1CC2)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H](C(CC1)C(C)=C)[C@@]21NCCN(CC1)CCS1(=O)=O)CC(O)=O Chemical compound CC(C)(CCC(C(C)(C)[C@@H]1CC2)=CC[C@]1(C)[C@@H](CC1)[C@]2(C)[C@](C)(CC2)[C@H]1[C@@H](C(CC1)C(C)=C)[C@@]21NCCN(CC1)CCS1(=O)=O)CC(O)=O VPFDJYDFKGJMOA-QAYJEQJRSA-N 0.000 description 1
- ZGUVYMUXBOYSFG-ZXZMAJKNSA-N CC(C)([C@H](CC1)[C@](C)(CC2)[C@@H](CC3)[C@]1(C)[C@](C)(CC1)C3[C@@H]([C@@H](CC3)C(C)=C)C13N=O)C2=O Chemical compound CC(C)([C@H](CC1)[C@](C)(CC2)[C@@H](CC3)[C@]1(C)[C@](C)(CC1)C3[C@@H]([C@@H](CC3)C(C)=C)C13N=O)C2=O ZGUVYMUXBOYSFG-ZXZMAJKNSA-N 0.000 description 1
- JGLKZKFJJXZEEL-SKEMKGFNSA-N CC(C)([C@H](CC1)[C@](C)(CC2)[C@@H](CC3)[C@]1(C)[C@](C)(CC1)[C@H]3[C@@H]([C@@H](CC3)C(C)=C)[C@@]13N=O)[C@H]2O Chemical compound CC(C)([C@H](CC1)[C@](C)(CC2)[C@@H](CC3)[C@]1(C)[C@](C)(CC1)[C@H]3[C@@H]([C@@H](CC3)C(C)=C)[C@@]13N=O)[C@H]2O JGLKZKFJJXZEEL-SKEMKGFNSA-N 0.000 description 1
- ZTUADFKTEYCTGR-LBDLRSOWSA-N CC(C)([C@H](CC1)[C@](C)(CC2)[C@@H](CC3)[C@]1(C)[C@](C)(CCC(CC1)([C@@H]4[C@@H]1C(C)=C)N=O)[C@]34N)[C@H]2O Chemical compound CC(C)([C@H](CC1)[C@](C)(CC2)[C@@H](CC3)[C@]1(C)[C@](C)(CCC(CC1)([C@@H]4[C@@H]1C(C)=C)N=O)[C@]34N)[C@H]2O ZTUADFKTEYCTGR-LBDLRSOWSA-N 0.000 description 1
- FHPQVXSNTGZBDY-BSUYWYSUSA-N CC(C)[C@H](CC1)[C@H]([C@@H](CC2)[C@@](C)(CC3)[C@](C)(CC4)C2[C@]2(C)[C@@H]4C(C)(C)C(CCCCCC(O)=O)CC2)C13NCCN(CCC=1)CC[S]=1(=O)=O Chemical compound CC(C)[C@H](CC1)[C@H]([C@@H](CC2)[C@@](C)(CC3)[C@](C)(CC4)C2[C@]2(C)[C@@H]4C(C)(C)C(CCCCCC(O)=O)CC2)C13NCCN(CCC=1)CC[S]=1(=O)=O FHPQVXSNTGZBDY-BSUYWYSUSA-N 0.000 description 1
- IGNGFGXAWDQJGP-UHFFFAOYSA-N CC1CN(C)CC1 Chemical compound CC1CN(C)CC1 IGNGFGXAWDQJGP-UHFFFAOYSA-N 0.000 description 1
- RVZGPAFPYOIKKF-UHFFFAOYSA-O CCCN(CCC=[OH+])CCN Chemical compound CCCN(CCC=[OH+])CCN RVZGPAFPYOIKKF-UHFFFAOYSA-O 0.000 description 1
- KFWWGWYYAJBJBL-VBUYDJLRSA-N CCC[C@](C)([C@H](CC1)[C@](C)(CC2(C)C)CC=C2/C=C\C=C\C(O)=O)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21NCCN1CCC(C)CC1 Chemical compound CCC[C@](C)([C@H](CC1)[C@](C)(CC2(C)C)CC=C2/C=C\C=C\C(O)=O)[C@](C)(CC2)[C@H]1[C@@H]([C@@H](CC1)C(C)=C)[C@@]21NCCN1CCC(C)CC1 KFWWGWYYAJBJBL-VBUYDJLRSA-N 0.000 description 1
- RFWAAXNLVJXFQD-UHFFFAOYSA-N CN(CC1)CCC1N1CCN(C)CC1 Chemical compound CN(CC1)CCC1N1CCN(C)CC1 RFWAAXNLVJXFQD-UHFFFAOYSA-N 0.000 description 1
- FZYSZYWKHFCLSF-UHFFFAOYSA-N CN(CC1)CCNC1=O Chemical compound CN(CC1)CCNC1=O FZYSZYWKHFCLSF-UHFFFAOYSA-N 0.000 description 1
- ULZCOWMSBOJCLT-UHFFFAOYSA-N CN(CC1)CCS1(=O)=O Chemical compound CN(CC1)CCS1(=O)=O ULZCOWMSBOJCLT-UHFFFAOYSA-N 0.000 description 1
- FQKYGXLDOAFGCC-UHFFFAOYSA-N CN(CCN1)C(CC(O)=O)C1=O Chemical compound CN(CCN1)C(CC(O)=O)C1=O FQKYGXLDOAFGCC-UHFFFAOYSA-N 0.000 description 1
- KVIZTDNKHOCNAM-UHFFFAOYSA-N CN(CCN1)CC1=O Chemical compound CN(CCN1)CC1=O KVIZTDNKHOCNAM-UHFFFAOYSA-N 0.000 description 1
- UWOHOTTUMMONTJ-UHFFFAOYSA-N CN(CCN1C2CCCC2)CC1=O Chemical compound CN(CCN1C2CCCC2)CC1=O UWOHOTTUMMONTJ-UHFFFAOYSA-N 0.000 description 1
- XKRADRXZXCDDHA-UHFFFAOYSA-N CN(CCNC1)CC1O Chemical compound CN(CCNC1)CC1O XKRADRXZXCDDHA-UHFFFAOYSA-N 0.000 description 1
- PAMIQIKDUOTOBW-UHFFFAOYSA-N CN1CCCCC1 Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 1
- SJRJJKPEHAURKC-UHFFFAOYSA-N CN1CCOCC1 Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 1
- KDTVWEHAAISPNW-UHFFFAOYSA-N CN1CCSCC1 Chemical compound CN1CCSCC1 KDTVWEHAAISPNW-UHFFFAOYSA-N 0.000 description 1
- VIVZKIVQZAFASA-UHFFFAOYSA-N NCCN(CC1)CCS1(O)=O Chemical compound NCCN(CC1)CCS1(O)=O VIVZKIVQZAFASA-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
- C07J53/002—Carbocyclic rings fused
-
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- A61K31/568—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
-
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Molecular Biology (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361768630P | 2013-02-25 | 2013-02-25 | |
| US61/768,630 | 2013-02-25 | ||
| PCT/US2014/017688 WO2014130810A1 (en) | 2013-02-25 | 2014-02-21 | C-3 alkyl and alkenyl modified betulinic acid derivatives useful in the treatment of hiv |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN105102468A true CN105102468A (zh) | 2015-11-25 |
Family
ID=50288267
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201480010426.3A Pending CN105102468A (zh) | 2013-02-25 | 2014-02-21 | 用于治疗hiv的c-3烷基和烯基修饰的桦木酸衍生物 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US9249180B2 (enExample) |
| EP (1) | EP2958930A1 (enExample) |
| JP (1) | JP6186012B2 (enExample) |
| KR (1) | KR20150121712A (enExample) |
| CN (1) | CN105102468A (enExample) |
| AR (1) | AR094876A1 (enExample) |
| AU (1) | AU2014218754B2 (enExample) |
| BR (1) | BR112015019590A2 (enExample) |
| CA (1) | CA2902513A1 (enExample) |
| EA (1) | EA027861B1 (enExample) |
| IL (1) | IL240739A0 (enExample) |
| MX (1) | MX2015010354A (enExample) |
| SG (1) | SG11201506445PA (enExample) |
| TW (1) | TW201444862A (enExample) |
| WO (1) | WO2014130810A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106749486A (zh) * | 2016-11-30 | 2017-05-31 | 沈阳化工大学 | 一种以乙二胺为连接臂的齐墩果酸衍生物及其应用 |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10202365B2 (en) | 2015-02-06 | 2019-02-12 | Blueprint Medicines Corporation | 2-(pyridin-3-yl)-pyrimidine derivatives as RET inhibitors |
| US10221208B2 (en) * | 2015-04-14 | 2019-03-05 | ViiV Healthcare UK (No.4) Limited | Methods of producing an HIV maturation inhibitor |
| EA038890B1 (ru) | 2015-11-02 | 2021-11-03 | Блюпринт Медсинс Корпорейшн | Ингибиторы ret |
| AR107512A1 (es) | 2016-02-04 | 2018-05-09 | VIIV HEALTHCARE UK Nº 5 LTD | Triterpenoides modificados en c-3 y c-17 como inhibidores del vih-1 |
| AR107912A1 (es) | 2016-03-17 | 2018-06-28 | Blueprint Medicines Corp | Inhibidores de ret |
| WO2018017983A1 (en) | 2016-07-22 | 2018-01-25 | Blueprint Medicines Corporation | Compounds useful for treating disorders related to ret |
| WO2018022761A1 (en) | 2016-07-27 | 2018-02-01 | Blueprint Medicines Corporation | Substituted cyclopentane-amides for treating disorders related to ret |
| WO2018044838A1 (en) * | 2016-08-31 | 2018-03-08 | Viiv Healthcare Company | Combinations and uses and treatments thereof |
| RU2020113341A (ru) | 2017-09-14 | 2021-10-15 | Феникс Байотекнолоджи, Инк. | Способ и композиция для лечения вирусной инфекции |
| EP3681477A4 (en) | 2017-09-14 | 2021-06-09 | Phoenix Biotechnology, Inc. | PROCEDURES AND IMPROVED COMPOSITION FOR TREATMENT OF TREITERPEN RESPONSIBLE CONDITIONS, DISEASES, OR DISORDERS |
| CA3096043A1 (en) | 2018-04-03 | 2019-10-10 | Blueprint Medicines Corporation | Ret inhibitor for use in treating cancer having a ret alteration |
| HRP20231582T1 (hr) | 2019-02-11 | 2024-03-15 | Hetero Labs Limited | Novi derivati triterpena kao inhibitori hiv-a |
| CN111440151A (zh) * | 2020-03-25 | 2020-07-24 | 魏威 | 制备抗肿瘤药普拉赛替尼的方法 |
| CN111362923A (zh) * | 2020-03-25 | 2020-07-03 | 魏威 | 制备ret抑制剂普拉塞替尼的方法、以及普拉塞替尼的中间体及其制备方法 |
| JP7153083B2 (ja) | 2020-03-31 | 2022-10-13 | フェニックス・バイオテクノロジー・インコーポレイテッド | コロナウイルス感染を治療するための方法および組成物 |
| EP4295854A3 (en) | 2020-03-31 | 2024-04-03 | Phoenix Biotechnology, Inc. | Method and compositions for treating coronavirus infection |
| KR20230017234A (ko) | 2020-05-29 | 2023-02-03 | 블루프린트 메디신즈 코포레이션 | 프랄세티닙의 고체 형태 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6369101B1 (en) * | 1999-02-26 | 2002-04-09 | Regents Of The University Of Minnesota | Therapeutic method to treat herpes virus infection |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5413999A (en) | 1991-11-08 | 1995-05-09 | Merck & Co., Inc. | HIV protease inhibitors useful for the treatment of AIDS |
| US5679828A (en) | 1995-06-05 | 1997-10-21 | Biotech Research Labs, Inc. | Betulinic acid and dihydrobetulinic acid derivatives and uses therefor |
| US20020137755A1 (en) | 2000-12-04 | 2002-09-26 | Bilodeau Mark T. | Tyrosine kinase inhibitors |
| US20040110785A1 (en) | 2001-02-02 | 2004-06-10 | Tao Wang | Composition and antiviral activity of substituted azaindoleoxoacetic piperazine derivatives |
| US7365221B2 (en) | 2002-09-26 | 2008-04-29 | Panacos Pharmaceuticals, Inc. | Monoacylated betulin and dihydrobetulin derivatives, preparation thereof and use thereof |
| US7745625B2 (en) | 2004-03-15 | 2010-06-29 | Bristol-Myers Squibb Company | Prodrugs of piperazine and substituted piperidine antiviral agents |
| MXPA06010592A (es) | 2004-03-17 | 2007-06-12 | Panacos Pharmaceuticals Inc | Sales farmaceuticas de acido 3-o-(3',3'-dimetilsuccinil) betulinico. |
| TW200628161A (en) | 2004-11-12 | 2006-08-16 | Panacos Pharmaceuticals Inc | Novel betulin derivatives, preparation thereof and use thereof |
| US20110144069A1 (en) | 2006-10-16 | 2011-06-16 | Myriad Genetics, Incorporated | Compounds for treating viral infections |
| EP2257567A1 (en) | 2008-02-14 | 2010-12-08 | Virochem Pharma Inc. | Novel 17 beta lupane derivatives |
| US9067966B2 (en) | 2009-07-14 | 2015-06-30 | Hetero Research Foundation, Hetero Drugs Ltd. | Lupeol-type triterpene derivatives as antivirals |
| CN103038245B (zh) * | 2010-06-04 | 2015-03-25 | 百时美施贵宝公司 | 作为hiv成熟抑制剂的c-3经修饰的桦木酸衍生物 |
| MX2012013628A (es) | 2010-06-04 | 2012-12-17 | Bristol Myers Squibb Co | Amidas c-28 de derivados del acido betulinico c-3 modificados como inhibidores de la maduracion del virus de inmunodeficiencia humana (vih). |
| US8846647B2 (en) | 2011-01-31 | 2014-09-30 | Bristol-Myers Squibb Company | C-17 and C-3 modified triterpenoids with HIV maturation inhibitory activity |
| RS54352B1 (sr) | 2011-01-31 | 2016-02-29 | Bristol-Myers Squibb Company | C-28 amini c-3 modifikovanih derivata betulinske kiseline kao inhibitori sazrevanja hiv-a |
| US8889854B2 (en) | 2012-05-07 | 2014-11-18 | Bristol-Myers Squibb Company | C-17 bicyclic amines of triterpenoids with HIV maturation inhibitory activity |
-
2014
- 2014-02-21 MX MX2015010354A patent/MX2015010354A/es unknown
- 2014-02-21 EA EA201591545A patent/EA027861B1/ru not_active IP Right Cessation
- 2014-02-21 BR BR112015019590A patent/BR112015019590A2/pt not_active Application Discontinuation
- 2014-02-21 AU AU2014218754A patent/AU2014218754B2/en not_active Ceased
- 2014-02-21 CN CN201480010426.3A patent/CN105102468A/zh active Pending
- 2014-02-21 KR KR1020157026070A patent/KR20150121712A/ko not_active Withdrawn
- 2014-02-21 EP EP14710687.6A patent/EP2958930A1/en not_active Withdrawn
- 2014-02-21 SG SG11201506445PA patent/SG11201506445PA/en unknown
- 2014-02-21 WO PCT/US2014/017688 patent/WO2014130810A1/en not_active Ceased
- 2014-02-21 CA CA2902513A patent/CA2902513A1/en not_active Abandoned
- 2014-02-21 US US14/186,533 patent/US9249180B2/en not_active Expired - Fee Related
- 2014-02-21 JP JP2015558996A patent/JP6186012B2/ja not_active Expired - Fee Related
- 2014-02-24 TW TW103106131A patent/TW201444862A/zh unknown
- 2014-02-24 AR ARP140100580A patent/AR094876A1/es unknown
-
2015
- 2015-08-20 IL IL240739A patent/IL240739A0/en unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6369101B1 (en) * | 1999-02-26 | 2002-04-09 | Regents Of The University Of Minnesota | Therapeutic method to treat herpes virus infection |
Non-Patent Citations (2)
| Title |
|---|
| CHAO-MEI MA ET AL.: "CHEMICAL MODIFICATION OF OLEANENE TYPE TRITERPENES AND THEIR INHIBITORY ACTIVITY AGAINST HIV-1 PROTEASE DIMERIZATION", 《CHEM.PHARM.BULL》 * |
| YOSHIKI KASHIWADA ET AL.: "SYNTHESIS AND ANTI-HIV ACTIVITY OF 3-ALKYLAMIDO-3-DEOXY-BETULINIC ACID DERIVATIVES", 《CHEM.PHARM.BULL》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106749486A (zh) * | 2016-11-30 | 2017-05-31 | 沈阳化工大学 | 一种以乙二胺为连接臂的齐墩果酸衍生物及其应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| IL240739A0 (en) | 2015-10-29 |
| EP2958930A1 (en) | 2015-12-30 |
| SG11201506445PA (en) | 2015-09-29 |
| KR20150121712A (ko) | 2015-10-29 |
| EA027861B1 (ru) | 2017-09-29 |
| CA2902513A1 (en) | 2014-08-28 |
| TW201444862A (zh) | 2014-12-01 |
| US20140243298A1 (en) | 2014-08-28 |
| AR094876A1 (es) | 2015-09-02 |
| BR112015019590A2 (pt) | 2017-07-18 |
| EA201591545A1 (ru) | 2015-12-30 |
| WO2014130810A1 (en) | 2014-08-28 |
| AU2014218754A1 (en) | 2015-10-15 |
| MX2015010354A (es) | 2015-10-09 |
| JP6186012B2 (ja) | 2017-08-23 |
| US9249180B2 (en) | 2016-02-02 |
| AU2014218754B2 (en) | 2017-04-20 |
| JP2016509062A (ja) | 2016-03-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| WD01 | Invention patent application deemed withdrawn after publication | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20151125 |