CA2935898C - Composition and method for the protection of articular cartilage - Google Patents
Composition and method for the protection of articular cartilage Download PDFInfo
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- CA2935898C CA2935898C CA2935898A CA2935898A CA2935898C CA 2935898 C CA2935898 C CA 2935898C CA 2935898 A CA2935898 A CA 2935898A CA 2935898 A CA2935898 A CA 2935898A CA 2935898 C CA2935898 C CA 2935898C
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- articular cartilage
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- calebin
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- 210000001188 articular cartilage Anatomy 0.000 title claims abstract description 24
- 238000000034 method Methods 0.000 title abstract description 11
- 239000000203 mixture Substances 0.000 title abstract description 8
- 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 19
- 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 18
- 230000006378 damage Effects 0.000 claims abstract description 15
- 230000001575 pathological effect Effects 0.000 claims abstract description 13
- 241000124008 Mammalia Species 0.000 claims abstract description 6
- 239000003814 drug Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 abstract description 3
- 241000700159 Rattus Species 0.000 description 9
- 239000002671 adjuvant Substances 0.000 description 8
- 210000001519 tissue Anatomy 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 6
- 210000002683 foot Anatomy 0.000 description 6
- 210000005222 synovial tissue Anatomy 0.000 description 6
- 230000002917 arthritic effect Effects 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- 208000014674 injury Diseases 0.000 description 4
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 3
- 206010018691 Granuloma Diseases 0.000 description 3
- 229960001138 acetylsalicylic acid Drugs 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 230000008733 trauma Effects 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- WZUVPPKBWHMQCE-UHFFFAOYSA-N Haematoxylin Chemical compound C12=CC(O)=C(O)C=C2CC2(O)C1C1=CC=C(O)C(O)=C1OC2 WZUVPPKBWHMQCE-UHFFFAOYSA-N 0.000 description 2
- 241000187479 Mycobacterium tuberculosis Species 0.000 description 2
- 206010003246 arthritis Diseases 0.000 description 2
- 210000000548 hind-foot Anatomy 0.000 description 2
- 210000004698 lymphocyte Anatomy 0.000 description 2
- 230000002792 vascular Effects 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 208000009386 Experimental Arthritis Diseases 0.000 description 1
- 244000158441 Pleurotus sajor caju Species 0.000 description 1
- 235000004116 Pleurotus sajor caju Nutrition 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000003356 anti-rheumatic effect Effects 0.000 description 1
- 210000000544 articulatio talocruralis Anatomy 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 210000001612 chondrocyte Anatomy 0.000 description 1
- 210000002808 connective tissue Anatomy 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 description 1
- 230000002327 eosinophilic effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 206010020718 hyperplasia Diseases 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000000725 suspension 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
- A61K31/216—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
-
- 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
- A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
-
- 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
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Abstract
The novel therapeutic potential of Calebin A and compositions thereof to prevent pathological damage to mammalian articular cartilage is disclosed. Specifically a method has been provided for protecting mammalian articular cartilage from pathological damage, said method comprising the step of administering effective dose of Calebin A to mammals in need of said protection.
Description
COMPOSITION AND METHOD FOR THE PROTECTION OF ARTICULAR CARTILAGE
BACKGROUND OF THE INVENTION
[Para 001] Field of the invention [Para 002] The present invention in general pertains to protective compositions and methods thereof for articular cartilage. Specifically, the present invention pertains to the potential of Calebin A to prevent pathological damage to articular cartilage.
[Para 003] Description of prior art [Para 0041 Articular cartilage is a specialized connective tissue that covers the articular surfaces of bones forming a synovial joint. Articular cartilage endows the synovial joints the ability to provide low friction and relatively pain free motion. Articular cartilage structures and functions are prone to damage following trauma (fall or accident), wear and tear and underlying pathological disease conditions. Articular cartilage tissue usually does not regenerate (the process of self repair) after injury or disease leading to loss of tissue and formation of a defect.
Reasons attributed to such non-regeneration include (i) Fewer cellular components; (ii) poor metabolism and (iii) the restricted capacity of innate chondrocytes to divide and migrate in the tissue on account of dense matrix fibers. Thus, active principles that are capable of protecting articular cartilage from damage due to trauma and disease constitute important technological areas that offer considerable scope to improve the quality of life of individuals who are prone to such trauma.
[Para 005] It is the principle of the present invention to disclose the potential of Calebin A and compositions thereof to prevent pathological damage to mammalian articular cartilage.
[Para 006] The present invention fulfills the aforesaid objective and provides further related advantages.
SUMMARY OF THE INVENTION
[Para 0071 The present invention relates to the potential of Calebin A and compositions thereof to prevent pathological damage to mammalian articular cartilage.
[Para 008] The present invention provides the following advantage.
1. Disclosure of the novel therapeutic potential of Calebin A and compositions thereof to prevent pathological damage to mammalian articular cartilage.
[Para 009] Other features and advantages of the present invention will become apparent from the following more detailed description, taken in conjunction with the accompanying images, which illustrate, by way of example, the principle of the invention.
BRIEF DESCRIPTION OF THE FIGURES
[Para 0010] Fig.1 shows the histopathology of the rat paw tissue section of arthritic control group.
[Para 0011] Fig.2 shows the histopathology of the rat paw tissue section of the group treated with Calebin A (10 mg/kg).
[Para 0012] Fig.3 shows the histopathology of the rat paw tissue section of the group treated with Calebin A (20 mg/kg).
DETAILED DESCRIPTION OF THE MOST PREFERRED EMBODIMENT
(Figs.1, 2 and 3) [Para 0013] In the most preferred embodiment, the present invention relates to a method of using Calebin A in effective amounts to protect mammalian articular cartilage from pathological damage, said method comprising the step of administering effective dose of Calebin A to mammals in need of said protection.
[Para 0014] In another preferred embodiment, the present invention relates to the method of protecting mammalian articular cartilage from pathological damage, said method comprising the step of administering effective dose of Calebin A to mammals in need of said protection.
[Para 0015] The novel therapeutic potential of Calebin A and compositions thereof to prevent pathological damage to mammalian articular cartilage is clearly enunciated in the illustrative examples discussed herein below.
[Para 0016] Illustrative Example 1 [Para 0017] Pathological damage: Adjuvant induced arthritis in animal models [Para 0018] Animals used: Albino Wistar rats of either sex [Para 0019] Weight of the animals: 140-180 grams [Para 0020] Number of animals/group: 05 [Para 0021] Methodology: Chronic arthritis was induced in rats by the injection of 0.05mL of (0.5% w/v) suspension of killed Mycobacterium tuberculosis, homogenized in liquid paraffin in the left hind foot.
Table A
Scheme of work for screening of Calebin A in Mycobacterium tuberculosis (adjuvant) induced arthritis in mammals Animal Group Test compound Treatment Group 1 Naïve control Vehicle Group 2 Arthritic control Vehicle + 0.5% w/v adjuvant
BACKGROUND OF THE INVENTION
[Para 001] Field of the invention [Para 002] The present invention in general pertains to protective compositions and methods thereof for articular cartilage. Specifically, the present invention pertains to the potential of Calebin A to prevent pathological damage to articular cartilage.
[Para 003] Description of prior art [Para 0041 Articular cartilage is a specialized connective tissue that covers the articular surfaces of bones forming a synovial joint. Articular cartilage endows the synovial joints the ability to provide low friction and relatively pain free motion. Articular cartilage structures and functions are prone to damage following trauma (fall or accident), wear and tear and underlying pathological disease conditions. Articular cartilage tissue usually does not regenerate (the process of self repair) after injury or disease leading to loss of tissue and formation of a defect.
Reasons attributed to such non-regeneration include (i) Fewer cellular components; (ii) poor metabolism and (iii) the restricted capacity of innate chondrocytes to divide and migrate in the tissue on account of dense matrix fibers. Thus, active principles that are capable of protecting articular cartilage from damage due to trauma and disease constitute important technological areas that offer considerable scope to improve the quality of life of individuals who are prone to such trauma.
[Para 005] It is the principle of the present invention to disclose the potential of Calebin A and compositions thereof to prevent pathological damage to mammalian articular cartilage.
[Para 006] The present invention fulfills the aforesaid objective and provides further related advantages.
SUMMARY OF THE INVENTION
[Para 0071 The present invention relates to the potential of Calebin A and compositions thereof to prevent pathological damage to mammalian articular cartilage.
[Para 008] The present invention provides the following advantage.
1. Disclosure of the novel therapeutic potential of Calebin A and compositions thereof to prevent pathological damage to mammalian articular cartilage.
[Para 009] Other features and advantages of the present invention will become apparent from the following more detailed description, taken in conjunction with the accompanying images, which illustrate, by way of example, the principle of the invention.
BRIEF DESCRIPTION OF THE FIGURES
[Para 0010] Fig.1 shows the histopathology of the rat paw tissue section of arthritic control group.
[Para 0011] Fig.2 shows the histopathology of the rat paw tissue section of the group treated with Calebin A (10 mg/kg).
[Para 0012] Fig.3 shows the histopathology of the rat paw tissue section of the group treated with Calebin A (20 mg/kg).
DETAILED DESCRIPTION OF THE MOST PREFERRED EMBODIMENT
(Figs.1, 2 and 3) [Para 0013] In the most preferred embodiment, the present invention relates to a method of using Calebin A in effective amounts to protect mammalian articular cartilage from pathological damage, said method comprising the step of administering effective dose of Calebin A to mammals in need of said protection.
[Para 0014] In another preferred embodiment, the present invention relates to the method of protecting mammalian articular cartilage from pathological damage, said method comprising the step of administering effective dose of Calebin A to mammals in need of said protection.
[Para 0015] The novel therapeutic potential of Calebin A and compositions thereof to prevent pathological damage to mammalian articular cartilage is clearly enunciated in the illustrative examples discussed herein below.
[Para 0016] Illustrative Example 1 [Para 0017] Pathological damage: Adjuvant induced arthritis in animal models [Para 0018] Animals used: Albino Wistar rats of either sex [Para 0019] Weight of the animals: 140-180 grams [Para 0020] Number of animals/group: 05 [Para 0021] Methodology: Chronic arthritis was induced in rats by the injection of 0.05mL of (0.5% w/v) suspension of killed Mycobacterium tuberculosis, homogenized in liquid paraffin in the left hind foot.
Table A
Scheme of work for screening of Calebin A in Mycobacterium tuberculosis (adjuvant) induced arthritis in mammals Animal Group Test compound Treatment Group 1 Naïve control Vehicle Group 2 Arthritic control Vehicle + 0.5% w/v adjuvant
2 Group 3 Acetyl salicylic acid (ASA) 100 ASA+0.5% w/v adjuvant mg/kg. (per oral) Calebin A
Group 4 2.5 mg/kg (per oral Test compound + 0.5% w/v administration) adjuvant Group 5 5 mg/kg (per oral Test compound + 0.5% w/v administration) adjuvant Group 6 10 mg/kg (per oral Test compound + 0.5% w/v administration) adjuvant Group 7 20 mg/kg (per oral Test compound + 0.5% w/v administration) adjuvant [Para 0022] Histopathology:
[Para 00231 Right ankle joints of the animals in the control and treated groups were separated from the hind paw, weighed and immersed in 10% buffered formalin for 24 hours, followed by decalcification in 10% EDTA, The joints were then dehydrated, processed and paraffin (56C-58C) blocks were prepared, stained (hematoxylin and eosin) and examined under the compound microscope (Patel P, Patel D, Patel N. Experimental investigation of anti-rheumatoid activity of Pleurotus sajorcaju in adjuvant-induced arthritic rats. Chinese Journal of Natural Medicines, 2012; 10 (4): 0269-0274.
[Para 0024] Histopathology results:
[Para 0025] The rat paw tissue of the control arthritic group showed (Fig.1) focally damaged articular cartilage with synovial tissue (Arrows). The articular cartilage and synovial tissue were replaced by abundant eosinophilic caeseous necrosis with scattered epitheloid cells and there were few poorly formed ill-defined granulomas.
[Para 0026] The rat paw tissue of the group treated with Calebin A (10 mg/kg) [Fig.2] showed intact articular cartilage with synovial tissue in the joint. The synovial tissue consisted of congested vascular spaces (Long-Arrows), scattered lymphocytes (Short-Arrow) and intact synovial lining. No granulomas were seen.
[Para 0027] The rat paw tissue of the group treated with Calebin A (20 mg/kg) [Fig.3] showed intact articular cartilage with synovial tissue in the joint. The synovial tissue consisted of mild synovial epithelial hyperplasia (Short-Arrow), scattered lymphocytes (Long-Arrow) and intact vascular spaces. No granulomas were seen.
[Para 0028] The histopathological studies of arthritic rats shows dose dependant protection of articular cartilage with Calebin A.
[Para 0029] While the invention has been described with reference to a preferred embodiment, it is to be clearly understood by those skilled in the art that the invention is not limited thereto.
Group 4 2.5 mg/kg (per oral Test compound + 0.5% w/v administration) adjuvant Group 5 5 mg/kg (per oral Test compound + 0.5% w/v administration) adjuvant Group 6 10 mg/kg (per oral Test compound + 0.5% w/v administration) adjuvant Group 7 20 mg/kg (per oral Test compound + 0.5% w/v administration) adjuvant [Para 0022] Histopathology:
[Para 00231 Right ankle joints of the animals in the control and treated groups were separated from the hind paw, weighed and immersed in 10% buffered formalin for 24 hours, followed by decalcification in 10% EDTA, The joints were then dehydrated, processed and paraffin (56C-58C) blocks were prepared, stained (hematoxylin and eosin) and examined under the compound microscope (Patel P, Patel D, Patel N. Experimental investigation of anti-rheumatoid activity of Pleurotus sajorcaju in adjuvant-induced arthritic rats. Chinese Journal of Natural Medicines, 2012; 10 (4): 0269-0274.
[Para 0024] Histopathology results:
[Para 0025] The rat paw tissue of the control arthritic group showed (Fig.1) focally damaged articular cartilage with synovial tissue (Arrows). The articular cartilage and synovial tissue were replaced by abundant eosinophilic caeseous necrosis with scattered epitheloid cells and there were few poorly formed ill-defined granulomas.
[Para 0026] The rat paw tissue of the group treated with Calebin A (10 mg/kg) [Fig.2] showed intact articular cartilage with synovial tissue in the joint. The synovial tissue consisted of congested vascular spaces (Long-Arrows), scattered lymphocytes (Short-Arrow) and intact synovial lining. No granulomas were seen.
[Para 0027] The rat paw tissue of the group treated with Calebin A (20 mg/kg) [Fig.3] showed intact articular cartilage with synovial tissue in the joint. The synovial tissue consisted of mild synovial epithelial hyperplasia (Short-Arrow), scattered lymphocytes (Long-Arrow) and intact vascular spaces. No granulomas were seen.
[Para 0028] The histopathological studies of arthritic rats shows dose dependant protection of articular cartilage with Calebin A.
[Para 0029] While the invention has been described with reference to a preferred embodiment, it is to be clearly understood by those skilled in the art that the invention is not limited thereto.
3 Rather, the scope of the invention is to be interpreted only in conjunction with the appended claims.
4
Claims (2)
1. Use of Calebin A in effective amounts to protect mammalian articular cartilage from pathological damage in a mammal in need of said protection.
2. Use of Calebin A for the manufacture of a medicament for protecting articular cartilage from pathological damage in a mammal in need of said protection.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US2014/010993 WO2015105501A1 (en) | 2014-01-10 | 2014-01-10 | Composition and method for the protection of articular cartilage |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2935898A1 CA2935898A1 (en) | 2015-07-16 |
| CA2935898C true CA2935898C (en) | 2018-11-06 |
Family
ID=53524213
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2935898A Active CA2935898C (en) | 2014-01-10 | 2014-01-10 | Composition and method for the protection of articular cartilage |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JP6142446B2 (en) |
| KR (2) | KR101685263B1 (en) |
| AU (1) | AU2014201769B2 (en) |
| CA (1) | CA2935898C (en) |
| EA (1) | EA027614B1 (en) |
| NZ (1) | NZ622909A (en) |
| PH (1) | PH12016501138B1 (en) |
| SG (1) | SG11201605336YA (en) |
| WO (1) | WO2015105501A1 (en) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6887898B1 (en) * | 1999-10-22 | 2005-05-03 | Darrick S. H. L. Kim | Pharmaceutical compositions useful in prevention and treatment of beta-Amyloid protein-induced disease |
| GB2439960B (en) | 2006-07-08 | 2011-11-16 | Redweb Security | Material for marking an article using DNA |
| EP2040696B1 (en) * | 2006-07-14 | 2017-01-25 | DSM IP Assets B.V. | Compositions and use thereof for the treatment, co-treatment or prevention of inflammatory disorders |
| US8577013B1 (en) | 2011-01-10 | 2013-11-05 | West Corporation | Automatic communications forwarding to displaced employees |
-
2014
- 2014-01-10 CA CA2935898A patent/CA2935898C/en active Active
- 2014-01-10 AU AU2014201769A patent/AU2014201769B2/en not_active Ceased
- 2014-01-10 JP JP2016516634A patent/JP6142446B2/en not_active Expired - Fee Related
- 2014-01-10 WO PCT/US2014/010993 patent/WO2015105501A1/en active Application Filing
- 2014-01-10 NZ NZ622909A patent/NZ622909A/en not_active IP Right Cessation
- 2014-01-10 EA EA201591212A patent/EA027614B1/en unknown
- 2014-01-10 KR KR1020147009279A patent/KR101685263B1/en active IP Right Grant
- 2014-01-10 SG SG11201605336YA patent/SG11201605336YA/en unknown
- 2014-01-10 KR KR1020167014135A patent/KR101685333B1/en active IP Right Grant
-
2016
- 2016-06-13 PH PH12016501138A patent/PH12016501138B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SG11201605336YA (en) | 2016-07-28 |
| KR20160087387A (en) | 2016-07-21 |
| AU2014201769A1 (en) | 2015-07-30 |
| JP2016520126A (en) | 2016-07-11 |
| EA027614B1 (en) | 2017-08-31 |
| PH12016501138A1 (en) | 2016-07-18 |
| KR101685333B1 (en) | 2016-12-09 |
| AU2014201769B2 (en) | 2018-05-24 |
| WO2015105501A1 (en) | 2015-07-16 |
| NZ622909A (en) | 2018-04-27 |
| CA2935898A1 (en) | 2015-07-16 |
| PH12016501138B1 (en) | 2016-07-18 |
| KR20150105185A (en) | 2015-09-16 |
| EA201591212A1 (en) | 2015-10-30 |
| KR101685263B1 (en) | 2016-12-09 |
| JP6142446B2 (en) | 2017-06-07 |
| EA201591212A8 (en) | 2016-05-31 |
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| Date | Code | Title | Description |
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| EEER | Examination request |
Effective date: 20160729 |