CN103764641B - 部分饱和的三环化合物及其制备和使用方法 - Google Patents
部分饱和的三环化合物及其制备和使用方法 Download PDFInfo
- Publication number
- CN103764641B CN103764641B CN201280033359.8A CN201280033359A CN103764641B CN 103764641 B CN103764641 B CN 103764641B CN 201280033359 A CN201280033359 A CN 201280033359A CN 103764641 B CN103764641 B CN 103764641B
- Authority
- CN
- China
- Prior art keywords
- chromene
- carboxylic acid
- 7bsr
- 1ars
- tetrahydrocyclopropane
- 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.)
- Expired - Fee Related
Links
- 0 CC1(*)C=COCC1(*)* Chemical compound CC1(*)C=COCC1(*)* 0.000 description 11
- XISZPNMGFHMQON-UHFFFAOYSA-N CC(C)(C)OC(N(C(OC(C)(C)C)=O)c1c(C(OC)=O)c(OSc2ccc(C)cc2)ccc1)=O Chemical compound CC(C)(C)OC(N(C(OC(C)(C)C)=O)c1c(C(OC)=O)c(OSc2ccc(C)cc2)ccc1)=O XISZPNMGFHMQON-UHFFFAOYSA-N 0.000 description 1
- YQWJXKXYDUNPGP-UHFFFAOYSA-N CC(C)(C)OC(N(C1)CC1c1cccc(F)c1)=O Chemical compound CC(C)(C)OC(N(C1)CC1c1cccc(F)c1)=O YQWJXKXYDUNPGP-UHFFFAOYSA-N 0.000 description 1
- XNDNBWFUKMQQCX-UHFFFAOYSA-N CC(C)(C)OC(N(CC1)CC1OCC(C(C=C1)S(Cl)(=O)=O)C=C1F)=O Chemical compound CC(C)(C)OC(N(CC1)CC1OCC(C(C=C1)S(Cl)(=O)=O)C=C1F)=O XNDNBWFUKMQQCX-UHFFFAOYSA-N 0.000 description 1
- MJIKMYJGZCZECP-KHSQXAGFSA-N CC(C)(C)O[IH](N(CC1)C[C@@H]1OCc(cc(cc1)F)c1S(N(C)c1c(C(OC)=O)c(OC[C@H]2[C@@H]3C2)c3cc1)=O)=O Chemical compound CC(C)(C)O[IH](N(CC1)C[C@@H]1OCc(cc(cc1)F)c1S(N(C)c1c(C(OC)=O)c(OC[C@H]2[C@@H]3C2)c3cc1)=O)=O MJIKMYJGZCZECP-KHSQXAGFSA-N 0.000 description 1
- NLVOJIKOULHWIP-UHFFFAOYSA-N CC1CC(F)=CC(CN(C)C(C(F)(F)F)=O)=C(C)C1 Chemical compound CC1CC(F)=CC(CN(C)C(C(F)(F)F)=O)=C(C)C1 NLVOJIKOULHWIP-UHFFFAOYSA-N 0.000 description 1
- OFPPJOSAYFDRFK-CLFYSBASSA-M CCN(C)C/C=C\c(cccc1)c1S([N-]c1ccc(C(C2)C2CO2)c2c1C(OC)=O)(=O)=O Chemical compound CCN(C)C/C=C\c(cccc1)c1S([N-]c1ccc(C(C2)C2CO2)c2c1C(OC)=O)(=O)=O OFPPJOSAYFDRFK-CLFYSBASSA-M 0.000 description 1
- ZTMVHLCRBRHLGA-WAYWQWQTSA-N CCN(CC)C/C=C\c1c(CNC2=CCC(C(C3CO4)C3(F)F)C4=C2C(O)=O)ccc(F)c1 Chemical compound CCN(CC)C/C=C\c1c(CNC2=CCC(C(C3CO4)C3(F)F)C4=C2C(O)=O)ccc(F)c1 ZTMVHLCRBRHLGA-WAYWQWQTSA-N 0.000 description 1
- YTPCLGSFCBHDBZ-GYWYDZQHSA-N CCN(CC1)CC1C(C)CCC(C/C(/C=C(\C)/F)=C(/C)\S(CNc1c(C2=[O][C@H]2O)c(OCC2C3C2)c3cc1)=N)=O Chemical compound CCN(CC1)CC1C(C)CCC(C/C(/C=C(\C)/F)=C(/C)\S(CNc1c(C2=[O][C@H]2O)c(OCC2C3C2)c3cc1)=N)=O YTPCLGSFCBHDBZ-GYWYDZQHSA-N 0.000 description 1
- GOLVGZOPWLLUSF-LURJTMIESA-N CCN(CC1)C[C@H]1N Chemical compound CCN(CC1)C[C@H]1N GOLVGZOPWLLUSF-LURJTMIESA-N 0.000 description 1
- PKJXIIULUVRYOL-UHFFFAOYSA-N CCN1CC(CN(C(O)OC(C)C(C)C)C(OC(C)(C)C)=O)C1 Chemical compound CCN1CC(CN(C(O)OC(C)C(C)C)C(OC(C)(C)C)=O)C1 PKJXIIULUVRYOL-UHFFFAOYSA-N 0.000 description 1
- QKMYEKUXLYPHBG-MRVPVSSYSA-N CCN1C[C@H](CC#N)CC1 Chemical compound CCN1C[C@H](CC#N)CC1 QKMYEKUXLYPHBG-MRVPVSSYSA-N 0.000 description 1
- OSDOHDPAFPNPCV-WAYWQWQTSA-N CCNC/C=C\c(cc(cc1)F)c1S(NC(C1C(OC)=O)=CC=C2C1(C)OCC1C2C1)(=O)=O Chemical compound CCNC/C=C\c(cc(cc1)F)c1S(NC(C1C(OC)=O)=CC=C2C1(C)OCC1C2C1)(=O)=O OSDOHDPAFPNPCV-WAYWQWQTSA-N 0.000 description 1
- DFQBLAFVPCPNRJ-YBUBMKCBSA-N CC[N-](CCC1)[C@H]1C(N(C)Cc(cc(cc1)F)c1S([C@@H](C)c1c(C(O)=O)c(OCC2C3C2)c3cc1)(=C)=O)=O Chemical compound CC[N-](CCC1)[C@H]1C(N(C)Cc(cc(cc1)F)c1S([C@@H](C)c1c(C(O)=O)c(OCC2C3C2)c3cc1)(=C)=O)=O DFQBLAFVPCPNRJ-YBUBMKCBSA-N 0.000 description 1
- URAOWNSMLORSRE-UHFFFAOYSA-N Cc1c(C2C(CO)C2)ccc(N)c1C(OC)=O Chemical compound Cc1c(C2C(CO)C2)ccc(N)c1C(OC)=O URAOWNSMLORSRE-UHFFFAOYSA-N 0.000 description 1
- ZXAPMANOWGBURM-UHFFFAOYSA-N Fc1cc(CC2CCNCC2)ccc1 Chemical compound Fc1cc(CC2CCNCC2)ccc1 ZXAPMANOWGBURM-UHFFFAOYSA-N 0.000 description 1
- FQVVJFIHGLIEBJ-UHFFFAOYSA-N O=C(c1ccccc1S(Cl)(=O)=O)Cl Chemical compound O=C(c1ccccc1S(Cl)(=O)=O)Cl FQVVJFIHGLIEBJ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/94—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
-
- 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
- A61K31/4355—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 oxygen as a ring hetero atom
-
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Cardiology (AREA)
- Child & Adolescent Psychology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161483257P | 2011-05-06 | 2011-05-06 | |
| US61/483,257 | 2011-05-06 | ||
| US201161559856P | 2011-11-15 | 2011-11-15 | |
| US61/559,856 | 2011-11-15 | ||
| PCT/US2012/036789 WO2012154676A1 (en) | 2011-05-06 | 2012-05-07 | Partially saturated tricyclic compounds and methods of making and using same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103764641A CN103764641A (zh) | 2014-04-30 |
| CN103764641B true CN103764641B (zh) | 2016-10-26 |
Family
ID=46147038
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201280033359.8A Expired - Fee Related CN103764641B (zh) | 2011-05-06 | 2012-05-07 | 部分饱和的三环化合物及其制备和使用方法 |
Country Status (14)
| Country | Link |
|---|---|
| US (3) | US9290472B2 (enExample) |
| EP (1) | EP2705030B1 (enExample) |
| JP (1) | JP6062423B2 (enExample) |
| KR (1) | KR101979039B1 (enExample) |
| CN (1) | CN103764641B (enExample) |
| AU (1) | AU2012253757B2 (enExample) |
| BR (1) | BR112013028534A2 (enExample) |
| CA (1) | CA2835261C (enExample) |
| EA (1) | EA025526B1 (enExample) |
| IL (1) | IL229246A (enExample) |
| MX (1) | MX345535B (enExample) |
| PH (1) | PH12013502261A1 (enExample) |
| SG (1) | SG194812A1 (enExample) |
| WO (1) | WO2012154676A1 (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8642650B2 (en) | 2008-12-04 | 2014-02-04 | Zafgen, Inc. | Methods of treating an overweight or obese subject |
| WO2010065877A2 (en) | 2008-12-04 | 2010-06-10 | Zafgen Corporation | Methods of treating an overweight or obese subject |
| AU2010303270A1 (en) | 2009-10-09 | 2012-05-03 | Zafgen Corporation | Sulphone compounds for use in the treatment of obesity |
| US8815309B2 (en) | 2010-01-08 | 2014-08-26 | Zafgen, Inc. | Methods of treating a subject with benign prostate hyperplasia |
| MX343135B (es) | 2010-01-08 | 2016-10-25 | Zafgen Corp * | Compuestos de tipo fumagilol y métodos de realización y uso de los mismos. |
| WO2011127304A2 (en) | 2010-04-07 | 2011-10-13 | Zafgen Corporation | Methods of treating an overweight subject |
| WO2012012642A1 (en) | 2010-07-22 | 2012-01-26 | Zafgen Corporation | Tricyclic compounds and methds of making and using same |
| JP5913333B2 (ja) | 2010-10-12 | 2016-04-27 | ザフゲン，インコーポレイテッド | スルホンアミド化合物、およびそれを製造し使用する方法 |
| CA2819251A1 (en) | 2010-11-29 | 2012-06-07 | Zafgen Corporation | Treatment of obesity using non-daily administration of 6 - 0 - (4 - dimethylaminoethoxy) cinnamoyl fumagillol |
| WO2012103333A1 (en) | 2011-01-26 | 2012-08-02 | Zafgen Corporation | Tetrazole compounds and methods of making and using same |
| JP5876513B2 (ja) | 2011-03-08 | 2016-03-02 | ザフゲン，インコーポレイテッド | オキサスピロ［２．５］オクタン誘導体および類似体 |
| US9290472B2 (en) | 2011-05-06 | 2016-03-22 | Zafgen, Inc. | Partially saturated tricyclic compounds and methods of making and using same |
| BR112013028665A2 (pt) | 2011-05-06 | 2016-09-06 | Zafgen Inc | compostos de sulfonamida tricíclicos e métodos para fazer e usar os mesmos |
| CN103764652B (zh) | 2011-05-06 | 2016-03-23 | 扎夫根股份有限公司 | 三环吡唑磺酰胺化合物及其制备和使用方法 |
| EP2763671A2 (en) | 2011-10-03 | 2014-08-13 | Zafgen, Inc. | Methods of treating age related disorders |
| CA2861381A1 (en) | 2012-01-18 | 2013-07-25 | Zafgen, Inc. | Tricyclic sulfone compounds and methods of making and using same |
| CA2861390A1 (en) | 2012-01-18 | 2013-07-25 | Zafgen, Inc. | Tricyclic sulfonamide compounds and methods of making and using same |
| MX2014013599A (es) | 2012-05-08 | 2015-05-11 | Zafgen Inc | Tratamiento de la obesidad hipotalamica con inhibidores de metap2. |
| US9573918B2 (en) | 2012-05-09 | 2017-02-21 | Zafgen, Inc. | Fumigillol compounds and methods of making and using same |
| NZ707773A (en) * | 2012-11-05 | 2019-05-31 | Zafgen Inc | Methods of treating liver diseases |
| KR20150080614A (ko) | 2012-11-05 | 2015-07-09 | 자프겐 인크. | 비만의 치료 및/또는 제어에서 사용하기 위한 트리시클릭 화합물 |
| MX2015005732A (es) * | 2012-11-05 | 2015-12-16 | Zafgen Inc | Compuestos tricíclicos y métodos para hacer y utilizar los mismos. |
| BR112015023390A2 (pt) | 2013-03-14 | 2017-07-18 | Zafgen Inc | métodos para tratar de doença renal e outros distúrbios |
| AR105671A1 (es) | 2015-08-11 | 2017-10-25 | Zafgen Inc | Compuestos heterocíclicos de fumagillol y sus métodos de elaboración y uso |
| CN106432255A (zh) | 2015-08-11 | 2017-02-22 | 扎夫根公司 | 烟曲霉素醇螺环化合物和制备和使用其的方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010065883A2 (en) * | 2008-12-04 | 2010-06-10 | Zafgen Corporation | Method of treating an overweight or obese subject |
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| MX2013012921A (es) | 2014-02-27 |
| JP2014514349A (ja) | 2014-06-19 |
| BR112013028534A2 (pt) | 2016-09-06 |
| CA2835261A1 (en) | 2012-11-15 |
| EA201391644A1 (ru) | 2014-11-28 |
| AU2012253757A1 (en) | 2013-11-21 |
| AU2012253757A8 (en) | 2015-10-22 |
| US9617237B2 (en) | 2017-04-11 |
| KR20140047611A (ko) | 2014-04-22 |
| EP2705030B1 (en) | 2016-07-27 |
| CN103764641A (zh) | 2014-04-30 |
| WO2012154676A1 (en) | 2012-11-15 |
| US20170001973A1 (en) | 2017-01-05 |
| IL229246A (en) | 2017-05-29 |
| PH12013502261A1 (en) | 2022-10-26 |
| AU2012253757B2 (en) | 2017-04-13 |
| EP2705030A1 (en) | 2014-03-12 |
| MX345535B (es) | 2017-02-03 |
| US20140088078A1 (en) | 2014-03-27 |
| NZ617388A (en) | 2015-11-27 |
| WO2012154676A9 (en) | 2014-03-27 |
| US9290472B2 (en) | 2016-03-22 |
| SG194812A1 (en) | 2013-12-30 |
| IL229246A0 (en) | 2014-01-30 |
| KR101979039B1 (ko) | 2019-05-15 |
| JP6062423B2 (ja) | 2017-01-18 |
| CA2835261C (en) | 2019-06-04 |
| US20180002307A1 (en) | 2018-01-04 |
| EA025526B1 (ru) | 2017-01-30 |
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