CA2914997C - 4-alkynyl imidazole derivative and medicine comprising same as active ingredient - Google Patents

4-alkynyl imidazole derivative and medicine comprising same as active ingredient Download PDF

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Publication number
CA2914997C
CA2914997C CA2914997A CA2914997A CA2914997C CA 2914997 C CA2914997 C CA 2914997C CA 2914997 A CA2914997 A CA 2914997A CA 2914997 A CA2914997 A CA 2914997A CA 2914997 C CA2914997 C CA 2914997C
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Canada
Prior art keywords
group
mmol
compound
atom
added
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CA2914997A
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English (en)
French (fr)
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CA2914997A1 (en
Inventor
Satoru Ikegami
Atsushi Watanabe
Kimio HIRANO
Tadashi Ohyama
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Kaken Pharmaceutical Co Ltd
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Kaken Pharmaceutical Co Ltd
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Publication of CA2914997A1 publication Critical patent/CA2914997A1/en
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • A61K31/4164—1,3-Diazoles
    • 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
    • A61K31/4164—1,3-Diazoles
    • A61K31/4174—Arylalkylimidazoles, e.g. oxymetazolin, naphazoline, miconazole
    • 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
    • A61K31/4164—1,3-Diazoles
    • A61K31/4178—1,3-Diazoles not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
    • 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
    • A61K31/4245—Oxadiazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
    • 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
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • 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
    • 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
    • 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
    • A61P19/04—Drugs for skeletal disorders for non-specific disorders of the connective tissue
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic 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
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Immunology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Pain & Pain Management (AREA)
  • Neurosurgery (AREA)
  • Dermatology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Rheumatology (AREA)
  • Pulmonology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
CA2914997A 2013-06-12 2014-06-12 4-alkynyl imidazole derivative and medicine comprising same as active ingredient Active CA2914997C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP2013123968 2013-06-12
JP2013-123968 2013-06-12
PCT/JP2014/065643 WO2014200075A1 (ja) 2013-06-12 2014-06-12 ４－アルキニルイミダゾール誘導体およびそれを有効成分として含有する医薬

Publications (2)

Publication Number Publication Date
CA2914997A1 CA2914997A1 (en) 2014-12-18
CA2914997C true CA2914997C (en) 2021-07-20

Family

ID=52022361

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2914997A Active CA2914997C (en) 2013-06-12 2014-06-12 4-alkynyl imidazole derivative and medicine comprising same as active ingredient

Country Status (28)

Country Link
US (2) US9593081B2 (show.php)
EP (1) EP3009426B1 (show.php)
JP (1) JP6276760B2 (show.php)
KR (1) KR102212981B1 (show.php)
CN (1) CN105431416B (show.php)
AU (1) AU2014279113B2 (show.php)
BR (1) BR112015030315B1 (show.php)
CA (1) CA2914997C (show.php)
DK (1) DK3009426T3 (show.php)
ES (1) ES2669977T3 (show.php)
HR (1) HRP20180703T1 (show.php)
HU (1) HUE039015T2 (show.php)
IL (1) IL242912A0 (show.php)
LT (1) LT3009426T (show.php)
MX (1) MX369804B (show.php)
MY (1) MY168609A (show.php)
NO (1) NO3009426T3 (show.php)
NZ (1) NZ715837A (show.php)
PH (1) PH12015502745B1 (show.php)
PL (1) PL3009426T3 (show.php)
PT (1) PT3009426T (show.php)
RS (1) RS57406B1 (show.php)
RU (1) RU2662806C2 (show.php)
SG (1) SG11201510121RA (show.php)
SI (1) SI3009426T1 (show.php)
TR (1) TR201807659T4 (show.php)
WO (1) WO2014200075A1 (show.php)
ZA (1) ZA201600135B (show.php)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
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NO3009426T3 (show.php) * 2013-06-12 2018-09-29
CR20180323A (es) 2015-11-20 2018-08-06 Idorsia Pharmaceuticals Ltd Derivados de indol n-sustituídos como moduladores de los receptores de pge2
US20190276429A1 (en) * 2016-11-18 2019-09-12 Dow Agrosciencesllc 4-(6-(2-(2,4-difluorophenyl)-1.1-difluoro-2-hydroxy-3-(5-mercapto-1h-1,2,4-triazol-1-yl)propyl)pyridin-3-yl)oxy)benzonitrile and processes of preparation
AR111806A1 (es) 2017-05-18 2019-08-21 Idorsia Pharmaceuticals Ltd Derivados de indol n-sustituidos
HUE056382T2 (hu) 2017-05-18 2022-02-28 Idorsia Pharmaceuticals Ltd Pirimidin-származékok mint PGE2 receptor modulátorok
JP7253500B2 (ja) 2017-05-18 2023-04-06 イドーシア ファーマシューティカルズ リミテッド ピリミジン誘導体
AU2018269666B2 (en) 2017-05-18 2022-02-03 Idorsia Pharmaceuticals Ltd Phenyl derivatives as PGE2 receptor modulators
US11325899B2 (en) 2017-05-18 2022-05-10 Idorsia Pharmaceuticals Ltd Benzofurane and benzothiophene derivatives as PGE2 receptor modulators
WO2018216640A1 (ja) * 2017-05-22 2018-11-29 小野薬品工業株式会社 Ｅｐ４アンタゴニスト
JP2020142989A (ja) * 2017-06-21 2020-09-10 Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 イミダゾール誘導体及びそれを含有する医薬
EP3749323A4 (en) * 2018-02-05 2021-11-03 Shenzhen Ionova Life Science Co., Ltd. HETEROBICYCLIC CARBONIC ACIDS FOR TREATMENT OF CANCER OR INFLAMMATORY DISEASES
CN108997252B (zh) * 2018-07-27 2020-04-28 常州大学 一种恶二唑衍生物的绿色合成方法
KR20230107228A (ko) 2020-11-13 2023-07-14 오노 야꾸힝 고교 가부시키가이샤 Ep4 길항약과 면역 체크포인트 저해 물질의 병용에 의한 암 치료

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CA2436551A1 (en) 2001-01-31 2002-08-08 Pfizer Products Inc. Thiazolyl-, oxazolyl-, pyrrolyl-, and imidazolyl-acid amide derivatives useful as inhibitors of pde4 isozymes
NZ531153A (en) * 2001-08-09 2005-10-28 Ono Pharmaceutical Co Carboxylic acid derivative compounds and drugs comprising these compounds as the active ingredient
CN1662551A (zh) 2002-05-23 2005-08-31 瑟瑞技术公司 前列腺素e2受体亚型ep4的拮抗肽
BRPI0414130B8 (pt) 2003-09-03 2021-05-25 Askat Inc compostos de fenilamida ou piridilamida, seu uso e composições farmacêuticas que os compreendem.
CA2565813C (en) 2004-05-04 2010-10-26 Pfizer Inc. Substituted methyl aryl or heteroaryl amide compounds
JP4054369B2 (ja) 2004-05-04 2008-02-27 ファイザー株式会社 オルト置換アリールまたはヘテロアリールアミド化合物
BRPI0607439A2 (pt) * 2005-02-16 2010-04-06 Solvay Pharm Bv compostos, composição farmacêutica, método de preparação de composições farmacêuticas, e, uso de um composto
CA2648729A1 (en) 2006-04-24 2007-11-01 Merck Frosst Canada Ltd. Indole amide derivatives as ep4 receptor antagonists
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AU2007283404B2 (en) 2006-08-11 2013-04-18 Merck Canada Inc. Thiophenecarboxamide derivatives as EP4 receptor ligands
CN101622230B (zh) * 2007-02-26 2012-08-22 默克弗罗斯特加拿大有限公司 作为ep4受体拮抗剂的吲哚和二氢吲哚环丙基酰胺衍生物
RU2010103104A (ru) * 2007-07-02 2011-08-10 Ф.Хоффманн-Ля Рош Аг (Ch) Производные имидазола в качестве антагонистов рецептора ccr2
WO2009005076A1 (ja) 2007-07-03 2009-01-08 Astellas Pharma Inc. アミド化合物
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CN102149384B (zh) 2008-08-14 2014-08-20 南京奥昭生物科技有限公司 作为ep4受体拮抗剂的杂环酰胺衍生物
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Also Published As

Publication number Publication date
PT3009426T (pt) 2018-06-08
JPWO2014200075A1 (ja) 2017-02-23
MX2015017161A (es) 2016-04-06
RU2662806C2 (ru) 2018-07-31
NZ715837A (en) 2020-01-31
CN105431416B (zh) 2019-01-08
PH12015502745B1 (en) 2019-01-25
HRP20180703T1 (hr) 2018-06-15
EP3009426A4 (en) 2016-10-19
EP3009426B1 (en) 2018-05-02
IL242912A0 (en) 2016-02-01
AU2014279113B2 (en) 2018-04-12
CN105431416A (zh) 2016-03-23
PH12015502745A1 (en) 2016-03-14
ES2669977T3 (es) 2018-05-29
US9855257B2 (en) 2018-01-02
US20160130232A1 (en) 2016-05-12
BR112015030315A2 (pt) 2017-07-25
KR20160018745A (ko) 2016-02-17
CA2914997A1 (en) 2014-12-18
DK3009426T3 (en) 2018-05-28
BR112015030315B1 (pt) 2022-10-04
LT3009426T (lt) 2018-07-25
JP6276760B2 (ja) 2018-02-07
MX369804B (es) 2019-11-21
RU2015155585A (ru) 2017-07-17
SG11201510121RA (en) 2016-01-28
PL3009426T3 (pl) 2018-09-28
EP3009426A1 (en) 2016-04-20
HK1221215A1 (zh) 2017-05-26
US20170128431A1 (en) 2017-05-11
NO3009426T3 (show.php) 2018-09-29
SI3009426T1 (en) 2018-06-29
RS57406B1 (sr) 2018-09-28
KR102212981B1 (ko) 2021-02-04
MY168609A (en) 2018-11-14
US9593081B2 (en) 2017-03-14
WO2014200075A1 (ja) 2014-12-18
TR201807659T4 (tr) 2018-06-21
HUE039015T2 (hu) 2018-12-28
AU2014279113A1 (en) 2016-01-21
ZA201600135B (en) 2017-04-26

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EEER Examination request

Effective date: 20190530