WO2015124616A1 - Compositions containing extracts of curcuma longa and echinacea angustifolia which are useful to reduce peripheral inflammation and pain - Google Patents
Compositions containing extracts of curcuma longa and echinacea angustifolia which are useful to reduce peripheral inflammation and pain Download PDFInfo
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- WO2015124616A1 WO2015124616A1 PCT/EP2015/053399 EP2015053399W WO2015124616A1 WO 2015124616 A1 WO2015124616 A1 WO 2015124616A1 EP 2015053399 W EP2015053399 W EP 2015053399W WO 2015124616 A1 WO2015124616 A1 WO 2015124616A1
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- Prior art keywords
- extract
- compositions according
- echinacea
- curcumin
- spp
- Prior art date
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- 239000000284 extract Substances 0.000 title claims abstract description 42
- 239000000203 mixture Substances 0.000 title claims abstract description 42
- 244000133098 Echinacea angustifolia Species 0.000 title claims abstract description 18
- 235000014134 echinacea Nutrition 0.000 title claims abstract description 18
- 208000002193 Pain Diseases 0.000 title claims abstract description 17
- 230000002093 peripheral effect Effects 0.000 title claims abstract description 7
- 244000163122 Curcuma domestica Species 0.000 title description 8
- 206010061218 Inflammation Diseases 0.000 title description 3
- 235000003373 curcuma longa Nutrition 0.000 title description 3
- 230000004054 inflammatory process Effects 0.000 title description 3
- VFLDPWHFBUODDF-FCXRPNKRSA-N curcumin Chemical compound C1=C(O)C(OC)=CC(\C=C\C(=O)CC(=O)\C=C\C=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-FCXRPNKRSA-N 0.000 claims abstract description 63
- 229940109262 curcumin Drugs 0.000 claims abstract description 28
- 239000004148 curcumin Substances 0.000 claims abstract description 28
- VFLDPWHFBUODDF-UHFFFAOYSA-N diferuloylmethane Natural products C1=C(O)C(OC)=CC(C=CC(=O)CC(=O)C=CC=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-UHFFFAOYSA-N 0.000 claims abstract description 28
- 235000012754 curcumin Nutrition 0.000 claims abstract description 27
- 238000011282 treatment Methods 0.000 claims abstract description 17
- 241000949456 Zanthoxylum Species 0.000 claims abstract description 13
- 150000003904 phospholipids Chemical class 0.000 claims abstract description 8
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- 201000008482 osteoarthritis Diseases 0.000 claims abstract description 7
- 239000004480 active ingredient Substances 0.000 claims abstract description 6
- 230000002757 inflammatory effect Effects 0.000 claims abstract description 5
- 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 4
- 244000164439 Curcuma angustifolia Species 0.000 claims abstract 2
- 235000020694 echinacea extract Nutrition 0.000 claims description 10
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 4
- 244000089698 Zanthoxylum simulans Species 0.000 claims description 4
- 208000006820 Arthralgia Diseases 0.000 claims description 3
- 229940064972 echinacea angustifolia extract Drugs 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 238000011200 topical administration Methods 0.000 claims description 3
- 208000000112 Myalgia Diseases 0.000 claims description 2
- 239000001569 carbon dioxide Substances 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims description 2
- 208000013465 muscle pain Diseases 0.000 claims description 2
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 abstract description 6
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 abstract description 5
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- 238000011866 long-term treatment Methods 0.000 abstract description 4
- 230000009885 systemic effect Effects 0.000 abstract description 4
- 150000003431 steroids Chemical class 0.000 abstract description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical class CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 8
- 230000000202 analgesic effect Effects 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
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- 239000012675 alcoholic extract Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000002674 ointment Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 3
- 239000000902 placebo Substances 0.000 description 3
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- 229920002785 Croscarmellose sodium Polymers 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 229940035676 analgesics Drugs 0.000 description 2
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- 230000003110 anti-inflammatory effect Effects 0.000 description 2
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- 229960001681 croscarmellose sodium Drugs 0.000 description 2
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 2
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 235000021388 linseed oil Nutrition 0.000 description 2
- 239000000944 linseed oil Substances 0.000 description 2
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 2
- 239000001095 magnesium carbonate Substances 0.000 description 2
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
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- 239000000454 talc Substances 0.000 description 2
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
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- 102000009132 CB1 Cannabinoid Receptor Human genes 0.000 description 1
- 108010073366 CB1 Cannabinoid Receptor Proteins 0.000 description 1
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- 108010073376 CB2 Cannabinoid Receptor Proteins 0.000 description 1
- 235000003392 Curcuma domestica Nutrition 0.000 description 1
- 208000032131 Diabetic Neuropathies Diseases 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 208000003947 Knee Osteoarthritis Diseases 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 102000011040 TRPV Cation Channels Human genes 0.000 description 1
- 108010062740 TRPV Cation Channels Proteins 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- -1 aliphatic ethers Chemical class 0.000 description 1
- 238000010876 biochemical test Methods 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
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- 238000007796 conventional method Methods 0.000 description 1
- LBJNMUFDOHXDFG-UHFFFAOYSA-N copper;hydrate Chemical compound O.[Cu].[Cu] LBJNMUFDOHXDFG-UHFFFAOYSA-N 0.000 description 1
- 235000020241 curcumin extract Nutrition 0.000 description 1
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- 230000008034 disappearance Effects 0.000 description 1
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- 201000006549 dyspepsia Diseases 0.000 description 1
- 230000002875 effect on osteoarthritis Effects 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 206010016766 flatulence Diseases 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 208000021302 gastroesophageal reflux disease Diseases 0.000 description 1
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- 239000000499 gel Substances 0.000 description 1
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- 150000008134 glucuronides Chemical class 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- UBHWBODXJBSFLH-UHFFFAOYSA-N hexadecan-1-ol;octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO.CCCCCCCCCCCCCCCCCCO UBHWBODXJBSFLH-UHFFFAOYSA-N 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
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- 230000002427 irreversible effect Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
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- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- A61K36/88—Liliopsida (monocotyledons)
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- A61K36/9066—Curcuma, e.g. common turmeric, East Indian arrowroot or mango ginger
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- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
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Definitions
- the present invention relates to compositions containing, as their only active ingredients, an extract of Curcuma spp, optionally as curcumin in the form of a complex with phospholipids, and an extract selected from Echinacea spp extract or a lipophilic extract of Zanthoxylum spp, which are useful in the topical and systemic treatment of peripheral pain and of superficial and deep inflammatory and painful conditions.
- the compositions according to the invention are particularly effective in the treatment of osteoarthritis and rheumatoid arthritis in patients unable to tolerate long-term treatment with NSAIDs or steroids.
- Osteoarthritis is one of the major causes of physical disability in elderly people. As well as reducing the quality of life of millions of individuals all over the world, it also causes financial loss to both families and the community, because the costs of the care involved are very high.
- the lipophilic extracts of Echinacea angustifolia described in EP 0464298 are particularly effective in this respect, due to their high isobutylamide content.
- turmeric The roots and rhizomes of turmeric (Curcuma) have been used as spices in India since time immemorial, and are also used in many industrialised countries today. Its active constituent is curcumin, the yellow compound that constitutes the main ingredient of curry and other traditional Indian dishes.
- the uses described in traditional medicine include the treatment of indigestion, flatulence and diarrhoea, and especially of inflammatory conditions and joint pain after long-term treatment. Many of these traditional uses have been confirmed by in vitro biochemical tests or pharmacology.
- Curcumin is now one of the molecules most frequently investigated from the biochemical standpoint, and in recent years, as well as numerous publications of doubtful scientific value, controlled double-blind clinical trials have also been conducted according to the protocols of modern clinical pharmacology. Preliminary clinical trials have demonstrated the low bioavailability of the molecule, which is unstable at intestinal pH (half-life at pH 7 ⁇ 10 min), and its low oral absorption, which limit many of the applications indicated by the in vitro tests. Plasma concentrations of 50 ng are reported after administration of 12 g of compound, the secondary metabolites, glucuronides and sulphates also being measured.
- curcumin is poorly soluble in water and fats.
- compositions containing as the only active ingredients Curcuma spp extract and an extract selected from Echinacea spp extract or lipophilic extract of Zanthoxylum spp possess potent analgesic and antiinflammatory activity, which is greater than that found when the extracts are used separately.
- compositions containing phospholipid-complexed curcumin and lipophilic extracts of Echinacea angustifolia have been observed.
- the object of the invention is therefore compositions substantially consisting of an extract of Curcuma spp or curcumin, and an extract selected from Echinacea angustifolia extract or lipophilic extract of Zanthoxylum bungeanum, mixed with acceptable excipients.
- the invention relates in particular to compositions substantially consisting of an extract of Curcuma spp or curcumin, and an extract selected from Echinacea angustifolia extract or lipophilic extract of Zanthoxylum bungeanum, mixed with acceptable excipients.
- compositions according to the invention may be administered orally or topically.
- the compositions for oral administration will contain phospholipid-complexed curcumin in amounts ranging from 100 to 1000 mg, and Echinacea extract in amounts ranging from 1 to 200 mg, or alternatively lipophilic extract of Zanthoxylum spp. in amounts ranging from 5 to 25 mg per oral dose unit.
- the compositions for oral administration will contain 500 mg of phospholipid- complexed curcumin and 5 mg of Echinacea extract, or alternatively 10 mg of lipophilic extract of Zanthoxylum spp., per oral dose unit.
- the compositions for topical administration will contain phospholipid-complexed curcumin in amounts ranging from 0.1 to 0.5% by weight, and Echinacea extract in amounts ranging from 0.05 to 0.5% by weight, or alternatively lipophilic extract of Zanthoxylum spp in amounts ranging from 0.1 to 1% by weight.
- the compositions for topical administration will contain 0.2% by weight of phospholipid-complexed curcumin, and 0.2% by weight of Echinacea extract, or alternatively 0.5% by weight of lipophilic extract of Zanthoxylum spp.
- compositions according to the invention can be used to treat peripheral pain of all kinds, ranging from diabetic neuropathy to joint and muscle pain of various origins. It is particularly important that the compositions according to the invention do not cause side effects in the gastrointestinal tract, to allow its use by patients with gastric problems who are unable to tolerate NSAIDs.
- Lipophilic extracts of Echinacea spp can be obtained by extraction from the roots or rhizomes with alcohols, ketones or aliphatic ethers, or preferably with carbon dioxide under supercritical conditions in accordance with EP464298.
- Alcoholic extracts of Echinacea spp still containing a pharmacologically active amount of isobutylamides have proved effective provided that at least a minimal dose of 1 mg of isobutylamine complex is administered to the patient.
- the active clinical doses range from 0.5 mg to 10 mg, preferably 5 mg for a mean body weight of 70 Kg.
- the lipophilic extract of Zanthoxylum spp can be prepared in accordance with WO 00/02570.
- the compositions according to the invention provide almost immediate relief of patients' symptoms, with no need to use other medicaments. Patients with gastro-oesophageal reflux and at the pre -ulcerative stage are also able to take the compositions according to the invention.
- compositions according to the invention (combination of phospholipid-complexed curcumin and Echinacea extract) was compared with that of the individual ingredients administered separately to rats.
- the analgesic activity was evaluated with the tail-flick test in the rat. Before treatment, 3 basic measurements were conducted on the animals to ensure that they were suitable for the handling and apparatus involved. The parameters used were 15V of radiant heat and a 15-second cut-off (to prevent irreversible harm to the animals), with evaluation of the tail-flick. The animals were treated with 0.1 ml of ointment of the composition described in example 4, 5 cm from the base of the tail. The analgesic effect was measured 15 and 30 min. after administration.
- Example 1 40 patients suffering from bone disease of the knee with constant pain were randomised and treated with two tablets a day according to Example 1 , one in the morning and one in the evening, or with a placebo (consisting of the carrier only), or with the individual ingredients added to the placebo formulation at the same concentrations as in the formulation described in example 1.
- Efficacy was scored on an international analogue pain scale with scores from 0 to 10, 10 points indicating maximum pain and 0 the disappearance of pain. The effect was evaluated on the second day after administration of the tablet, in the mornings 60 and 120 minutes after treatment.
- Table 3 shows the results obtained, after treatment for up to three months with the composition according to the invention, on the global effect of osteoarthritis on the patients recruited, following the Karnofsky Scale for both selection and evaluation of efficacy ( J.Clin.Oncology 1984; 2: 187-193).
- the evaluation was conducted by measuring the distance travelled without pain, and with different degrees of pain, on a treadmill set to 3 Km/h and an inclination of 10%. 80 patients suffering from osteoarthritis of the knee were divided into two groups. After randomisation, one group was treated with the placebo and the other with the composition described in example 1. Pain was evaluated weekly during the treatment with the WOMAC index, and the humoral parameters, which constitute indexes of inflammatory parameters, were evaluated every month. (Table 4). Table 3. Results of distance travelled on treadmill
- compositions in the form of gels, creams and ointments have proved particularly useful in the topical treatment of peripheral pain and of superficial and deep inflammatory and painful conditions.
- the combination can be applied directly to the skin in the oil in which it is solubilised, or incorporated in creams or ointments suitable for administration.
- the treatment can be performed one to three times a day, applying a dose of 0.5-5 g of the topical formulation to the part of the body affected by the painful disorder.
- compositions according to the invention may be administered together with other substances having a useful or complementary activity.
- compositions according to the invention will be formulated according to conventional techniques, such as those described in "Remington's Pharmaceutical Handbook", Mack Publishing Co., N.Y., USA. The examples below further illustrate the invention.
- Example 1 Tablets containing phospholipid-complexed curcumin and lipophilic extract of Echinacea
- Example 3 Tablets containing phospholipid-complexed curcumin and alcoholic extract of Echinacea
- Example 4 Ointment containing phospholipid-complexed curcumin and lipophilic extract of Echinacea angustifolia
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Abstract
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Priority Applications (16)
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PL15709426T PL3107555T3 (en) | 2014-02-20 | 2015-02-18 | Compositions containing extracts of curcuma longa and echinacea angustifolia which are useful to reduce peripheral inflammation and pain |
RU2016133688A RU2677894C2 (en) | 2014-02-20 | 2015-02-18 | Compositions containing extracts of curcuma longa and echinacea angustifolia which are useful to reduce peripheral inflammation and pain |
SI201531247T SI3107555T1 (en) | 2014-02-20 | 2015-02-18 | Compositions containing extracts of curcuma longa and echinacea angustifolia which are useful to reduce peripheral inflammation and pain |
SG11201606831PA SG11201606831PA (en) | 2014-02-20 | 2015-02-18 | Compositions containing extracts of curcuma longa and echinacea angustifolia which are useful to reduce peripheral inflammation and pain |
AU2015220913A AU2015220913B2 (en) | 2014-02-20 | 2015-02-18 | Compositions containing extracts of Curcuma Longa and Echinacea angustifolia which are useful to reduce peripheral inflammation and pain |
BR112016018973-6A BR112016018973B1 (en) | 2014-02-20 | 2015-02-18 | composition and use of a composition |
ES15709426T ES2804324T3 (en) | 2014-02-20 | 2015-02-18 | Compositions containing extracts of Curcuma longa and Echinacea angustifolia that are useful for reducing peripheral inflammation and pain |
KR1020167022484A KR102350519B1 (en) | 2014-02-20 | 2015-02-18 | Compositions containing extracts of Curcuma longa and Echinacea angustifolia which are useful to reduce peripheral inflammation and pain |
JP2016552578A JP6510544B2 (en) | 2014-02-20 | 2015-02-18 | Composition useful for alleviation of peripheral inflammation as well as pain comprising turmeric and extract of Fossula lengis |
CN201580009045.8A CN106029082A (en) | 2014-02-20 | 2015-02-18 | Compositions containing extracts of curcuma longa and echinacea angustifolia which are useful to reduce peripheral inflammation and pain |
CA2939976A CA2939976C (en) | 2014-02-20 | 2015-02-18 | Compositions containing extracts of curcuma longa and echinacea angustifolia which are useful to reduce peripheral inflammation and pain |
DK15709426.9T DK3107555T3 (en) | 2014-02-20 | 2015-02-18 | Compositions containing extracts of curcuma longa and echinacea angustifolia which are useful in reducing peripheral inflammation and pain |
US15/118,861 US10286028B2 (en) | 2014-02-20 | 2015-02-18 | Compositions containing extracts of Curcuma longa and Echinacea angustifolia which are useful to reduce peripheral inflammation and pain |
MX2016010722A MX2016010722A (en) | 2014-02-20 | 2015-02-18 | Compositions containing extracts of curcuma longa and echinacea angustifolia which are useful to reduce peripheral inflammation and pain. |
EP15709426.9A EP3107555B1 (en) | 2014-02-20 | 2015-02-18 | Compositions containing extracts of curcuma longa and echinacea angustifolia which are useful to reduce peripheral inflammation and pain |
IL247314A IL247314B (en) | 2014-02-20 | 2016-08-17 | Compositions containing extracts of curcuma longa and echinacea angustifolia which are useful to reduce peripheral inflammation and pain |
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US (1) | US10286028B2 (en) |
EP (1) | EP3107555B1 (en) |
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BR (1) | BR112016018973B1 (en) |
CA (1) | CA2939976C (en) |
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ES (1) | ES2804324T3 (en) |
HU (1) | HUE051696T2 (en) |
IL (1) | IL247314B (en) |
MX (1) | MX2016010722A (en) |
PL (1) | PL3107555T3 (en) |
PT (1) | PT3107555T (en) |
RU (1) | RU2677894C2 (en) |
SG (1) | SG11201606831PA (en) |
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Cited By (5)
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EP3150214A1 (en) * | 2015-10-01 | 2017-04-05 | INDENA S.p.A. | Compositions containing extracts of curcuma spp and zingiber officinale which are useful to reduce peripheral inflammation and pain |
WO2017103946A2 (en) | 2015-12-16 | 2017-06-22 | Parachur Vivek Anand | Tri-molecular complex of natural compounds |
ITUB20161030A1 (en) * | 2016-02-24 | 2017-08-24 | Indena Spa | USEFUL COMPOSITIONS IN PREVENTION AND / OR IN THE TREATMENT OF INFLAMMATION AND PAIN |
ITUA20164757A1 (en) * | 2016-06-29 | 2017-12-29 | Indena Spa | USEFUL COMPOSITIONS IN THE PREVENTION AND / OR IN THE TREATMENT OF INFLAMMATION AND OSTEOARTICULAR PAIN AND PAPER DAMAGE |
US10744174B1 (en) * | 2016-03-16 | 2020-08-18 | Robert Alonso | Composition(s) and method(s) for topically treating pain |
Families Citing this family (2)
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JP6987528B2 (en) * | 2017-05-12 | 2022-01-05 | 小林製薬株式会社 | Curcuminoid-containing tablets |
KR102020667B1 (en) * | 2017-09-29 | 2019-09-10 | 유씨엘 주식회사 | Cosmetic composition for preventing seborrheic dematitis and hair loss |
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2015
- 2015-02-18 MX MX2016010722A patent/MX2016010722A/en active IP Right Grant
- 2015-02-18 RU RU2016133688A patent/RU2677894C2/en active
- 2015-02-18 DK DK15709426.9T patent/DK3107555T3/en active
- 2015-02-18 EP EP15709426.9A patent/EP3107555B1/en active Active
- 2015-02-18 HU HUE15709426A patent/HUE051696T2/en unknown
- 2015-02-18 PT PT157094269T patent/PT3107555T/en unknown
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- 2015-02-18 BR BR112016018973-6A patent/BR112016018973B1/en active IP Right Grant
- 2015-02-18 WO PCT/EP2015/053399 patent/WO2015124616A1/en active Application Filing
- 2015-02-18 KR KR1020167022484A patent/KR102350519B1/en active IP Right Grant
- 2015-02-18 AU AU2015220913A patent/AU2015220913B2/en active Active
- 2015-02-18 SI SI201531247T patent/SI3107555T1/en unknown
- 2015-02-18 JP JP2016552578A patent/JP6510544B2/en active Active
- 2015-02-18 US US15/118,861 patent/US10286028B2/en active Active
- 2015-02-18 ES ES15709426T patent/ES2804324T3/en active Active
- 2015-02-18 CN CN201580009045.8A patent/CN106029082A/en active Pending
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IL247314B (en) | 2020-08-31 |
US10286028B2 (en) | 2019-05-14 |
KR20160113631A (en) | 2016-09-30 |
DK3107555T3 (en) | 2020-08-10 |
RU2016133688A (en) | 2018-03-23 |
RU2016133688A3 (en) | 2018-08-30 |
SI3107555T1 (en) | 2020-07-31 |
IL247314A0 (en) | 2016-09-29 |
CN106029082A (en) | 2016-10-12 |
PT3107555T (en) | 2020-07-10 |
ES2804324T3 (en) | 2021-02-05 |
EP3107555A1 (en) | 2016-12-28 |
JP2017506241A (en) | 2017-03-02 |
RU2677894C2 (en) | 2019-01-22 |
SG11201606831PA (en) | 2016-09-29 |
HUE051696T2 (en) | 2021-03-29 |
PL3107555T3 (en) | 2020-11-30 |
KR102350519B1 (en) | 2022-01-14 |
JP6510544B2 (en) | 2019-05-08 |
MX2016010722A (en) | 2016-11-10 |
CA2939976C (en) | 2023-09-05 |
US20170049840A1 (en) | 2017-02-23 |
EP3107555B1 (en) | 2020-06-03 |
AU2015220913A1 (en) | 2016-09-01 |
AU2015220913B2 (en) | 2020-04-09 |
CA2939976A1 (en) | 2015-08-27 |
BR112016018973B1 (en) | 2021-01-19 |
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