CA2963383C - Method for the treatment of hypercholesterolemia - Google Patents
Method for the treatment of hypercholesterolemia Download PDFInfo
- Publication number
- CA2963383C CA2963383C CA2963383A CA2963383A CA2963383C CA 2963383 C CA2963383 C CA 2963383C CA 2963383 A CA2963383 A CA 2963383A CA 2963383 A CA2963383 A CA 2963383A CA 2963383 C CA2963383 C CA 2963383C
- Authority
- CA
- Canada
- Prior art keywords
- calebin
- fat
- density lipoproteins
- mammals
- group
- 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.)
- Active
Links
- 208000035150 Hypercholesterolemia Diseases 0.000 title claims abstract description 26
- 238000000034 method Methods 0.000 title abstract description 20
- UYEWRTKHKAVRDI-UHFFFAOYSA-N Calebin A Natural products C1=C(O)C(OC)=CC(C=CC(=O)COC(=O)C=CC=2C=C(OC)C(O)=CC=2)=C1 UYEWRTKHKAVRDI-UHFFFAOYSA-N 0.000 claims abstract description 64
- UYEWRTKHKAVRDI-ASVGJQBISA-N Calebin A Chemical compound C1=C(O)C(OC)=CC(\C=C\C(=O)COC(=O)\C=C\C=2C=C(OC)C(O)=CC=2)=C1 UYEWRTKHKAVRDI-ASVGJQBISA-N 0.000 claims abstract description 64
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims abstract description 62
- 241000124008 Mammalia Species 0.000 claims abstract description 38
- 108010010234 HDL Lipoproteins Proteins 0.000 claims abstract description 28
- 102000015779 HDL Lipoproteins Human genes 0.000 claims abstract description 28
- 108010007622 LDL Lipoproteins Proteins 0.000 claims abstract description 27
- 102000007330 LDL Lipoproteins Human genes 0.000 claims abstract description 27
- 210000004369 blood Anatomy 0.000 claims abstract description 26
- 239000008280 blood Substances 0.000 claims abstract description 26
- 235000012000 cholesterol Nutrition 0.000 claims abstract description 25
- 108010062497 VLDL Lipoproteins Proteins 0.000 claims abstract description 24
- 201000001320 Atherosclerosis Diseases 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 18
- 210000002966 serum Anatomy 0.000 abstract description 10
- 150000003626 triacylglycerols Chemical class 0.000 abstract description 10
- 238000007726 management method Methods 0.000 abstract description 5
- 230000001225 therapeutic effect Effects 0.000 abstract description 4
- 235000019197 fats Nutrition 0.000 description 70
- 235000009200 high fat diet Nutrition 0.000 description 59
- 241001465754 Metazoa Species 0.000 description 42
- 229930184164 Calebin Natural products 0.000 description 26
- 208000008589 Obesity Diseases 0.000 description 11
- 235000020824 obesity Nutrition 0.000 description 11
- 238000012360 testing method Methods 0.000 description 10
- 230000037396 body weight Effects 0.000 description 8
- 235000005911 diet Nutrition 0.000 description 8
- 230000037213 diet Effects 0.000 description 8
- 230000006698 induction Effects 0.000 description 8
- 102000009027 Albumins Human genes 0.000 description 7
- 108010088751 Albumins Proteins 0.000 description 7
- 108010082126 Alanine transaminase Proteins 0.000 description 6
- 108010003415 Aspartate Aminotransferases Proteins 0.000 description 6
- 102000004625 Aspartate Aminotransferases Human genes 0.000 description 6
- 102100036475 Alanine aminotransferase 1 Human genes 0.000 description 4
- 210000001367 artery Anatomy 0.000 description 4
- 208000006575 hypertriglyceridemia Diseases 0.000 description 4
- 238000007619 statistical method Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- 102000004895 Lipoproteins Human genes 0.000 description 3
- 108090001030 Lipoproteins Proteins 0.000 description 3
- 231100000460 acute oral toxicity Toxicity 0.000 description 3
- 239000003146 anticoagulant agent Substances 0.000 description 3
- 229940127219 anticoagulant drug Drugs 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 208000019622 heart disease Diseases 0.000 description 3
- 235000018102 proteins Nutrition 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 230000029058 respiratory gaseous exchange Effects 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N Alanine Chemical compound CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- 206010012735 Diarrhoea Diseases 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 208000031226 Hyperlipidaemia Diseases 0.000 description 2
- 238000008214 LDL Cholesterol Methods 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 238000000540 analysis of variance Methods 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 229940105329 carboxymethylcellulose Drugs 0.000 description 2
- 208000029078 coronary artery disease Diseases 0.000 description 2
- 210000004351 coronary vessel Anatomy 0.000 description 2
- 231100000673 dose–response relationship Toxicity 0.000 description 2
- 239000003651 drinking water Substances 0.000 description 2
- 235000020188 drinking water Nutrition 0.000 description 2
- 230000000260 hypercholesteremic effect Effects 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 230000037023 motor activity Effects 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 208000000103 Anorexia Nervosa Diseases 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- 206010008479 Chest Pain Diseases 0.000 description 1
- 244000164439 Curcuma angustifolia Species 0.000 description 1
- 206010011703 Cyanosis Diseases 0.000 description 1
- 208000004930 Fatty Liver Diseases 0.000 description 1
- 206010019708 Hepatic steatosis Diseases 0.000 description 1
- 206010020565 Hyperaemia Diseases 0.000 description 1
- 208000000563 Hyperlipoproteinemia Type II Diseases 0.000 description 1
- 102100024640 Low-density lipoprotein receptor Human genes 0.000 description 1
- 206010065673 Nephritic syndrome Diseases 0.000 description 1
- 206010033546 Pallor Diseases 0.000 description 1
- 206010033645 Pancreatitis Diseases 0.000 description 1
- 206010035039 Piloerection Diseases 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 206010039424 Salivary hypersecretion Diseases 0.000 description 1
- 206010043994 Tonic convulsion Diseases 0.000 description 1
- 206010044565 Tremor Diseases 0.000 description 1
- 206010045261 Type IIa hyperlipidaemia Diseases 0.000 description 1
- 206010048255 Zieve syndrome Diseases 0.000 description 1
- SOHDIMHLMCRILN-UHFFFAOYSA-N [K+].[K+].CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[NH-]CC[NH-] Chemical compound [K+].[K+].CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[NH-]CC[NH-] SOHDIMHLMCRILN-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 230000016571 aggressive behavior Effects 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000003143 atherosclerotic effect Effects 0.000 description 1
- 210000003403 autonomic nervous system Anatomy 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 230000002566 clonic effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000020940 control diet Nutrition 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 229950010030 dl-alanine Drugs 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 201000001386 familial hypercholesterolemia Diseases 0.000 description 1
- 208000010706 fatty liver disease Diseases 0.000 description 1
- 230000003636 fecal output Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000010903 husk Substances 0.000 description 1
- 230000006742 locomotor activity Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 230000003387 muscular Effects 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 238000001543 one-way ANOVA Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000037081 physical activity Effects 0.000 description 1
- 230000005371 pilomotor reflex Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- -1 polypropylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 238000001223 reverse osmosis Methods 0.000 description 1
- 208000026451 salivation Diseases 0.000 description 1
- 235000021003 saturated fats Nutrition 0.000 description 1
- 231100000240 steatosis hepatitis Toxicity 0.000 description 1
- 238000013517 stratification Methods 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 239000002349 well water Substances 0.000 description 1
Classifications
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/25—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids with polyoxyalkylated alcohols, e.g. esters of polyethylene glycol
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
-
- 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
-
- 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
- A61P3/06—Antihyperlipidemics
-
- 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Emergency Medicine (AREA)
- Diabetes (AREA)
- Epidemiology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Gastroenterology & Hepatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14/259,404 US9668999B2 (en) | 2014-04-23 | 2014-04-23 | Method for the treatment of hypercholesterolemia |
| US14/259,404 | 2014-04-23 | ||
| CA2850999A CA2850999C (en) | 2014-04-23 | 2014-05-01 | Method for the treatment of hypertriglyceridemia |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2850999A Division CA2850999C (en) | 2014-04-23 | 2014-05-01 | Method for the treatment of hypertriglyceridemia |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2963383A1 CA2963383A1 (en) | 2015-10-23 |
| CA2963383C true CA2963383C (en) | 2018-12-04 |
Family
ID=50828681
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2963383A Active CA2963383C (en) | 2014-04-23 | 2014-05-01 | Method for the treatment of hypercholesterolemia |
| CA2850999A Active CA2850999C (en) | 2014-04-23 | 2014-05-01 | Method for the treatment of hypertriglyceridemia |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2850999A Active CA2850999C (en) | 2014-04-23 | 2014-05-01 | Method for the treatment of hypertriglyceridemia |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US9668999B2 (enExample) |
| EP (1) | EP2937084B1 (enExample) |
| JP (1) | JP6263707B2 (enExample) |
| KR (1) | KR101647549B1 (enExample) |
| AU (1) | AU2014202312B2 (enExample) |
| CA (2) | CA2963383C (enExample) |
| EA (1) | EA027148B1 (enExample) |
| MY (1) | MY170067A (enExample) |
| PH (1) | PH12014000244B1 (enExample) |
| PL (1) | PL2937084T3 (enExample) |
| TW (1) | TWI622394B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG10201503805XA (en) * | 2015-04-19 | 2016-11-29 | Sabinsa Corp | Calebin A For Hepatic Steatosis |
| US9539232B1 (en) * | 2016-08-04 | 2017-01-10 | Muhammed Majeed | Calebin A for osteoporosis |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1060352C (zh) * | 1996-02-08 | 2001-01-10 | 袁克兴 | 降脂药及其制备方法 |
| US6811786B1 (en) * | 1999-04-01 | 2004-11-02 | Ganeden Biotech, Inc. | Methods for reducing cholesterol using Bacillus coagulans spores, systems and compositions |
| WO2001030335A2 (en) * | 1999-10-22 | 2001-05-03 | The Board Of Trustees Of The University Of Illinois | Pharmaceutical compositions useful in the prevention and treatment of beta-amyloid protein-induced disease |
| US20020012733A1 (en) | 2000-04-12 | 2002-01-31 | The Procter & Gamble Company | Compositions for reducing hypercholesterolemia and controlling of postprandial blood glucose and insulin levels |
| JP2005232059A (ja) * | 2004-02-18 | 2005-09-02 | Iichiro Shimomura | 低アディポネクチン血症予防・治療剤 |
| JP4834824B2 (ja) * | 2004-07-08 | 2011-12-14 | 独立行政法人産業技術総合研究所 | アディポネクチン産生増強剤 |
| JP2010018522A (ja) * | 2007-03-23 | 2010-01-28 | Hiroshima Univ | アディポネクチン産生促進剤 |
| JP5294165B2 (ja) * | 2007-03-23 | 2013-09-18 | ナガセケムテックス株式会社 | アディポネクチン上昇剤 |
| CN101301455A (zh) * | 2008-07-01 | 2008-11-12 | 崔井朝 | 一种治疗高脂血症的中药复方姜黄固体分散体 |
| JP2011063543A (ja) * | 2009-09-17 | 2011-03-31 | Kao Corp | アディポネクチン増加剤 |
| US8933121B2 (en) * | 2011-01-10 | 2015-01-13 | Sami Labs Limited | Anti-obesity potential of Calebin A |
-
2014
- 2014-04-23 US US14/259,404 patent/US9668999B2/en active Active
- 2014-04-29 AU AU2014202312A patent/AU2014202312B2/en not_active Ceased
- 2014-05-01 CA CA2963383A patent/CA2963383C/en active Active
- 2014-05-01 CA CA2850999A patent/CA2850999C/en active Active
- 2014-05-02 JP JP2014095457A patent/JP6263707B2/ja not_active Expired - Fee Related
- 2014-05-08 PL PL14167512T patent/PL2937084T3/pl unknown
- 2014-05-08 EP EP14167512.4A patent/EP2937084B1/en active Active
- 2014-06-10 KR KR1020140070179A patent/KR101647549B1/ko not_active Expired - Fee Related
- 2014-07-25 MY MYPI2014002207A patent/MY170067A/en unknown
- 2014-08-26 PH PH12014000244A patent/PH12014000244B1/en unknown
- 2014-09-03 TW TW103130375A patent/TWI622394B/zh not_active IP Right Cessation
- 2014-09-17 EA EA201491545A patent/EA027148B1/ru unknown
-
2015
- 2015-03-03 US US14/637,081 patent/US9610273B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| PL2937084T3 (pl) | 2017-05-31 |
| EP2937084B1 (en) | 2016-11-30 |
| TWI622394B (zh) | 2018-05-01 |
| AU2014202312B2 (en) | 2018-02-22 |
| AU2014202312A1 (en) | 2015-11-12 |
| MY170067A (en) | 2019-07-03 |
| NZ624269A (en) | 2014-12-24 |
| EP2937084A1 (en) | 2015-10-28 |
| HK1210590A1 (en) | 2016-04-29 |
| JP2015209424A (ja) | 2015-11-24 |
| TW201540295A (zh) | 2015-11-01 |
| US20150306059A1 (en) | 2015-10-29 |
| CA2850999C (en) | 2018-04-03 |
| CA2850999A1 (en) | 2015-10-23 |
| US9668999B2 (en) | 2017-06-06 |
| KR20150122552A (ko) | 2015-11-02 |
| JP6263707B2 (ja) | 2018-01-24 |
| US9610273B2 (en) | 2017-04-04 |
| PH12014000244A1 (en) | 2016-08-08 |
| US20150306060A1 (en) | 2015-10-29 |
| EA201491545A1 (ru) | 2015-10-30 |
| KR101647549B1 (ko) | 2016-08-10 |
| CA2963383A1 (en) | 2015-10-23 |
| PH12014000244B1 (en) | 2016-08-08 |
| EA027148B1 (ru) | 2017-06-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20170404 |