HRP20171060T1 - Nova sol 3-[(3-{[4-(morfolinilmetil)-1h-pirol-2-il]metilen}-2-okso-2,3-dihidro-1h-indol-5-il-il-)metil]-1,3-tiazolidin-2,4-dion, njihova priprava i formulacije koje ih sadržavaju - Google Patents
Nova sol 3-[(3-{[4-(morfolinilmetil)-1h-pirol-2-il]metilen}-2-okso-2,3-dihidro-1h-indol-5-il-il-)metil]-1,3-tiazolidin-2,4-dion, njihova priprava i formulacije koje ih sadržavaju Download PDFInfo
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- HRP20171060T1 HRP20171060T1 HRP20171060TT HRP20171060T HRP20171060T1 HR P20171060 T1 HRP20171060 T1 HR P20171060T1 HR P20171060T T HRP20171060T T HR P20171060TT HR P20171060 T HRP20171060 T HR P20171060T HR P20171060 T1 HRP20171060 T1 HR P20171060T1
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- Prior art keywords
- compound
- methyl
- indol
- dihydro
- oxo
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims 2
- 150000003839 salts Chemical class 0.000 title claims 2
- AREYWCZYVPSHGS-UHFFFAOYSA-N 3-[[3-[[4-(morpholin-4-ylmethyl)-1h-pyrrol-2-yl]methylidene]-2-oxo-1h-indol-5-yl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1CC1=CC=C(NC(=O)C2=CC=3NC=C(CN4CCOCC4)C=3)C2=C1 AREYWCZYVPSHGS-UHFFFAOYSA-N 0.000 title 1
- 238000009472 formulation Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 11
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- HLEPAHCDDMLYAE-UHFFFAOYSA-N methanesulfonic acid 3-[[3-[[4-(morpholin-4-ylmethyl)-1H-pyrrol-2-yl]methylidene]-2-oxo-1H-indol-5-yl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound CS(O)(=O)=O.O=C1CSC(=O)N1Cc1ccc2NC(=O)C(=Cc3cc(CN4CCOCC4)c[nH]3)c2c1 HLEPAHCDDMLYAE-UHFFFAOYSA-N 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 239000002244 precipitate Substances 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 239000007858 starting material Substances 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- 208000003174 Brain Neoplasms Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 229940079156 Proteasome inhibitor Drugs 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 206010039491 Sarcoma Diseases 0.000 claims 1
- 206010041067 Small cell lung cancer Diseases 0.000 claims 1
- 238000002441 X-ray diffraction Methods 0.000 claims 1
- 230000000340 anti-metabolite Effects 0.000 claims 1
- 229940100197 antimetabolite Drugs 0.000 claims 1
- 239000002256 antimetabolite Substances 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 229910002056 binary alloy Inorganic materials 0.000 claims 1
- 230000005540 biological transmission Effects 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 210000000481 breast Anatomy 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 210000001072 colon Anatomy 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- ONCCWDRMOZMNSM-FBCQKBJTSA-N compound Z Chemical compound N1=C2C(=O)NC(N)=NC2=NC=C1C(=O)[C@H]1OP(O)(=O)OC[C@H]1O ONCCWDRMOZMNSM-FBCQKBJTSA-N 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 201000004101 esophageal cancer Diseases 0.000 claims 1
- 239000000706 filtrate Substances 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 231100000024 genotoxic Toxicity 0.000 claims 1
- 230000001738 genotoxic effect Effects 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 229940043355 kinase inhibitor Drugs 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 201000007270 liver cancer Diseases 0.000 claims 1
- 208000014018 liver neoplasm Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 230000000394 mitotic effect Effects 0.000 claims 1
- 201000000050 myeloid neoplasm Diseases 0.000 claims 1
- 210000000496 pancreas Anatomy 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 claims 1
- 239000002574 poison Substances 0.000 claims 1
- 231100000614 poison Toxicity 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 239000003207 proteasome inhibitor Substances 0.000 claims 1
- 238000001959 radiotherapy Methods 0.000 claims 1
- 208000000587 small cell lung carcinoma Diseases 0.000 claims 1
Classifications
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- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Claims (14)
1. 3-[(3-{[4-(4-Morfolinilmetil)-lW-pirol-2-il] metilen}-2-okso-2,3-dihidro-lH-indol-5-il)metil]-l,3-tiazolidin-2,4-dion metansulfonat formule (II):
[image]
naznačen time, da oznaka
[image]
označava da dvostruka veza ima Z ili E konfiguraciju.
2. Spoj u skladu s patentnim zahtjevom 1, naznačen time, da je spoj Z izomer 3-[(3-{[4-(4-morfolinil-metil)-1H-pirol-2-il]metilen}-2-okso-2,3-dihidro-ltf-indol-5-il)metil]-l,3-tiazolidin-2,4-dion metansulfonata.
3. Spoj u skladu s patentnim zahtjevom 1 ili 2, naznačen time, da njegov rendgenski difrakcijski dijagram ima slijedeće vrijednosti Braggovog kuta 28 (izraženo u °±0,2) 12,86; 15,13; 15,50; 17,70; 18,25; 18,71; 20,11; 21,46; 21,67; 21,89; 22,29; 22,58; 24,57; 25,82; 26,33.
4. Spoj u skladu s patentnim zahtjevom 1 ili 2, naznačen time, da sadržava sljedeće parametre, temeljene na dijagramu praška provedenom na Panalvtical Xpert-Pro MPD difraktometru (s bakarnom antikatodom) u načinu prijenosa sa
rasponom kuteva 3-55 ° 2θ, s korakom od 0,017 ° i 35,5 s po koraku, koji omogućuje da se identificiraju sljedeći parametri kristala:
- parametri jedinične ćelije: a = 15,0958 (5) A,b = 18,4586 (6) A,c = 8,8269 (2) Å, β = 94,074 (1) °, γ = 90 °
- prostorna skupina: C 1 c 1 (9)
-volumen jedinične ćelije: Vjedinične ćelije = 2453,37600 Å3.
5. Postupak za dobivanje spoja formule (II) u skladu s patentnim zahtjevom 1, naznačen time, da se kao početni materijal koristi 3-[(3-{[4-(4-morfolinilmetil)-l/-/-pirol-2-il]metilen}-2-okso-2,3-dihidro-lA7-indol-5-il)metil]-l,3-tiazolidin-2,4-dion, koji se nalazi u otopini binarnog sustava otapalo/voda, u koji se dodaje 1 do 2 molarna ekvivalenta metansulfonske kiseline, koja se miješa do taloženja metansulfonata, koji se filtrira.
6. Postupak za dobivanje spoja formule (II) u skladu s patentnim zahtjevom 1, naznačen time, da se kao početni materijal koristi 3-[(3-{[4-(4-morfolinlmetil)-1H-pirol-2-il]metilen}-2-okso-2,3-dihidro-1H-indol-5-il)metil]-1,3-tiazolidin-2,4-dion hidroklorid, koji se otopi u binarnom sustavu otapalo/voda, čija pH vrijednost se podesi na 8 dodavanjem baze, sol koja se stvara ukloni se filtracijom, zatim se filtrat zagrijava i dodaje se metansulfonska kiselina, smjesa se miješa i hladi do taloženje metansulfonata, koji se filtrira.
7. Farmaceutski pripravak, naznačen time, da sadržava spoj formule (II) u skladu s bilo kojim od patentnih zahtjeva 1 do 4, u kombinaciji s jednom ili više farmaceutski prihvatljivih pomoćnih tvari.
8. Farmaceutski pripravak u skladu s patentnim zahtjevom 7, naznačen time, da je spoj formule (II) Z izomer 3-[(3-{[4-(4-morfolinilmetil)-1H-pirol-2-il]metilen}-2-okso-2,3-dihidro-1H-indol-5-il)metil]-l,3-tiazolidin-2,4-dion metansulfonata.
9. Farmaceutski pripravci u skladu s patentnim zahtjevom 7 ili 8, naznačeni time, da se koriste za proizvodnju lijekova za liječenje raka debelog crijeva, dojke, jetre, bubrega, mozga i jednjaka, melanoma, mijeloma, karcinoma jajnika, karcinoma pluća ne-malih stanica, karcinoma pluća malih stanica, raka prostate i raka
pankreasa, sarkoma.
10. Spoj formule (II) u skladu s bilo kojim od patentnih zahtjeva 1 do 4, naznačen time, da je u kombinaciji sa sredstvom protiv karcinoma odabranim između genotoksičnih sredstava, mitotskih otrova, antimetabolita, inhibitora proteazoma ili inhibitora kinaza.
11. Farmaceutski pripravak u skladu s patentnim zahtjevom 10, naznačen time, da je spoj formule (II) Z izomer 3-[(3-{[4-(4-morfolinilmetil)-1H-pirol-2-il]metilen}-2-okso-2,3-dihidro-1H-indol-5-il)metil]-l,3-tiazolidin-2,4-dion metansulfonata.
12. Uporaba kombinacije u skladu s patentnim zahtjevom 10 ili 11, naznačen time,
da se koristi za proizvodnju lijekova u liječenju karcinoma.
13. Spoj formule (II) u skladu s bilo kojim od patentnih zahtjeva 1 do 4, naznačen time, da se koristi u kombinaciji s radioterapijom u liječenju karcinoma.
14. Spoj formule (II) za upotrebu u skladu s patentnim zahtjevom 13, naznačen
time, da je to Z izomer 3-[(3-{[4-(4-morfolinilmetil)-1H-pirol-2-il] metilen}-2-okso-2,3- dihidro-1H-indol-5-il) metil]-l,3-tiazolidin-2,4-dion metansulfonata.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1356870A FR3008411B1 (fr) | 2013-07-12 | 2013-07-12 | Nouveau sel de la 3-[(3-{[4-(4-morpholinylmethyl)-1h-pyrrol-2-yl]methylene}-2-oxo-2,3-dihydro-1h-indol-5-yl)methyl]-1,3-thiazolidine-2,4-dione, sa preparation, et les formulations qui le contiennent |
| EP14758600.2A EP3019497B1 (fr) | 2013-07-12 | 2014-07-11 | Nouveau sel de la 3-[(3-{[4-(4-morpholinylméthyl)-1h-pyrrol-2-yl]méthylène}-2-oxo-2,3-dihydro-1h-indol-5-yl)méthyl]-1,3-thiazolidine-2,4-dione, sa préparation, et les formulations qui le contiennent |
| PCT/FR2014/051783 WO2015004395A1 (fr) | 2013-07-12 | 2014-07-11 | Nouveau sel de la 3-[(3-{[4-(4-morpholinylméthyl)-1h-pyrrol-2-yl]méthylène}-2-oxo-2,3-dihydro-1h-indol-5-yl)méthyl]-1,3-thiazolidine-2,4-dione, sa préparation, et les formulations qui le contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20171060T1 true HRP20171060T1 (hr) | 2017-10-06 |
Family
ID=50424327
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20171060TT HRP20171060T1 (hr) | 2013-07-12 | 2017-07-11 | Nova sol 3-[(3-{[4-(morfolinilmetil)-1h-pirol-2-il]metilen}-2-okso-2,3-dihidro-1h-indol-5-il-il-)metil]-1,3-tiazolidin-2,4-dion, njihova priprava i formulacije koje ih sadržavaju |
Country Status (47)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10245270B2 (en) * | 2013-07-12 | 2019-04-02 | Les Laboratoires Servier | Salt of 3-[(3-{[4-(4-morpholinylmethyl)-1H-pyrrol-2-yl]methylene}-2-oxo-2,3-dihydro-1H-indol-5-yl)methyl]-1,3-thiazolidine-2,4-dione, its preparation, and formulations containing it |
| FR3039401B1 (fr) | 2015-07-31 | 2018-07-13 | Les Laboratoires Servier | Nouvelle association entre le 3-[(3-{[4-(4-morpholinylmethyl)-1h-pyrrol-2-yl]methylene}-2-oxo-2,3-dihydro-1h-indol-5-yl)methyl]-1,3-thiazolidine-2,4-dione et un inhibiteur de la tyr kinase du egfr |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2399358C (en) * | 2000-02-15 | 2006-03-21 | Sugen, Inc. | Pyrrole substituted 2-indolinone protein kinase inhibitors |
| US6960590B2 (en) * | 2000-10-17 | 2005-11-01 | Merck & Co. Inc. | Orally active salts with tyrosine kinase activity |
| AR042586A1 (es) * | 2001-02-15 | 2005-06-29 | Sugen Inc | 3-(4-amidopirrol-2-ilmetiliden)-2-indolinona como inhibidores de la protein quinasa; sus composiciones farmaceuticas; un metodo para la modulacion de la actividad catalitica de la proteinquinasa; un metodo para tratar o prevenir una afeccion relacionada con la proteinquinasa |
| AU2002360753B2 (en) * | 2001-12-27 | 2008-08-21 | Theravance, Inc. | Indolinone derivatives useful as protein kinase inhibitors |
| MXPA06004438A (es) * | 2003-10-24 | 2006-06-20 | Schering Ag | Derivados de indolinona y su uso en el tratamiento de enfermedades como el cancer. |
| DK1959948T3 (da) * | 2005-12-05 | 2012-08-20 | Xenoport Inc | Levodopa prodrug-mesylat, sammensætninger deraf og anvendelser deraf |
| FR2948940B1 (fr) * | 2009-08-04 | 2011-07-22 | Servier Lab | Nouveaux derives dihydroindolones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
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2013
- 2013-07-12 FR FR1356870A patent/FR3008411B1/fr active Active
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2014
- 2014-06-26 UY UY0001035629A patent/UY35629A/es unknown
- 2014-06-29 JO JOP/2014/0205A patent/JO3292B1/ar active
- 2014-07-11 LT LTEP14758600.2T patent/LT3019497T/lt unknown
- 2014-07-11 CN CN201480038854.7A patent/CN105377843B/zh not_active Expired - Fee Related
- 2014-07-11 MY MYPI2016700018A patent/MY183197A/en unknown
- 2014-07-11 DK DK14758600.2T patent/DK3019497T3/en active
- 2014-07-11 UA UAA201600944A patent/UA114041C2/uk unknown
- 2014-07-11 EA EA201600101A patent/EA031526B1/ru not_active IP Right Cessation
- 2014-07-11 PE PE2015002679A patent/PE20160079A1/es unknown
- 2014-07-11 PT PT147586002T patent/PT3019497T/pt unknown
- 2014-07-11 AR ARP140102566A patent/AR096882A1/es unknown
- 2014-07-11 TN TN2015000566A patent/TN2015000566A1/fr unknown
- 2014-07-11 SI SI201430246A patent/SI3019497T1/sl unknown
- 2014-07-11 EP EP14758600.2A patent/EP3019497B1/fr active Active
- 2014-07-11 AU AU2014289059A patent/AU2014289059B2/en not_active Ceased
- 2014-07-11 RS RS20170461A patent/RS55945B1/sr unknown
- 2014-07-11 US US14/904,260 patent/US9925195B2/en not_active Expired - Fee Related
- 2014-07-11 JP JP2016524879A patent/JP6532459B2/ja not_active Expired - Fee Related
- 2014-07-11 MD MDA20160003A patent/MD4507C1/ro not_active IP Right Cessation
- 2014-07-11 SG SG11201510570YA patent/SG11201510570YA/en unknown
- 2014-07-11 TW TW105105577A patent/TW201630906A/zh unknown
- 2014-07-11 HU HUE14758600A patent/HUE032568T2/hu unknown
- 2014-07-11 PL PL14758600T patent/PL3019497T3/pl unknown
- 2014-07-11 GE GEAP201414051A patent/GEP201706712B/en unknown
- 2014-07-11 ME MEP-2017-149A patent/ME02735B/me unknown
- 2014-07-11 WO PCT/FR2014/051783 patent/WO2015004395A1/fr active Application Filing
- 2014-07-11 KR KR1020167003298A patent/KR20160030399A/ko active Application Filing
- 2014-07-11 TW TW103124019A patent/TWI554510B/zh not_active IP Right Cessation
- 2014-07-11 ES ES14758600.2T patent/ES2632570T3/es active Active
- 2014-07-11 RU RU2016104642A patent/RU2680826C9/ru not_active IP Right Cessation
- 2014-07-11 KR KR1020187006643A patent/KR20180028554A/ko not_active Application Discontinuation
- 2014-07-11 NZ NZ715841A patent/NZ715841A/en not_active IP Right Cessation
- 2014-07-11 MX MX2016000332A patent/MX360291B/es active IP Right Grant
- 2014-07-11 CA CA2916380A patent/CA2916380C/fr not_active Expired - Fee Related
- 2014-07-11 MA MA38759A patent/MA38759B1/fr unknown
- 2014-07-11 AP AP2016008976A patent/AP2016008976A0/xx unknown
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2016
- 2016-01-04 PH PH12016500017A patent/PH12016500017B1/en unknown
- 2016-01-06 CL CL2016000013A patent/CL2016000013A1/es unknown
- 2016-01-07 CR CR20160012A patent/CR20160012A/es unknown
- 2016-01-07 DO DO2016000005A patent/DOP2016000005A/es unknown
- 2016-01-10 IL IL243526A patent/IL243526B/en not_active IP Right Cessation
- 2016-01-11 NI NI201600009A patent/NI201600009A/es unknown
- 2016-01-11 GT GT201600004A patent/GT201600004A/es unknown
- 2016-01-12 SA SA516370388A patent/SA516370388B1/ar unknown
- 2016-01-12 CU CUP2016000005A patent/CU20160005A7/es unknown
- 2016-08-30 HK HK16110306.0A patent/HK1222172A1/zh unknown
- 2016-09-13 HK HK16110825.2A patent/HK1222655A1/zh not_active IP Right Cessation
-
2017
- 2017-07-04 CY CY20171100714T patent/CY1119259T1/el unknown
- 2017-07-11 HR HRP20171060TT patent/HRP20171060T1/hr unknown
-
2018
- 2018-02-14 US US15/896,273 patent/US20180207171A1/en not_active Abandoned
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