JP2017519015A - Ot−r活性に関する疾患を治療するための方法に有用な結晶質の(3z,5s)−5−(ヒドロキシメチル)−1−[(2’−メチル−1,1’−ビフェニル−4−イル)カルボニル]ピロリジン−3−オン о−メチルオキシム - Google Patents
Ot−r活性に関する疾患を治療するための方法に有用な結晶質の(3z,5s)−5−(ヒドロキシメチル)−1−[(2’−メチル−1,1’−ビフェニル−4−イル)カルボニル]ピロリジン−3−オン о−メチルオキシム Download PDFInfo
- Publication number
- JP2017519015A JP2017519015A JP2016573776A JP2016573776A JP2017519015A JP 2017519015 A JP2017519015 A JP 2017519015A JP 2016573776 A JP2016573776 A JP 2016573776A JP 2016573776 A JP2016573776 A JP 2016573776A JP 2017519015 A JP2017519015 A JP 2017519015A
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- biphenyl
- carbonyl
- hydroxymethyl
- crystalline
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
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
- A61K31/40—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/04—Drugs for genital or sexual disorders; Contraceptives for inducing labour or abortion; Uterotonics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/06—Antiabortive agents; Labour repressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/10—Drugs for disorders of the endocrine system of the posterior pituitary hormones, e.g. oxytocin, ADH
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Epidemiology (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Psychiatry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462020076P | 2014-07-02 | 2014-07-02 | |
| US62/020,076 | 2014-07-02 | ||
| PCT/EP2015/062881 WO2016000920A1 (en) | 2014-07-02 | 2015-06-10 | Crystalline (3z,5s)-5-(hydroxymethyl)-1-[(2'-methyl-1,1'-biphenyl-4-yl)carbonyl]pyrrolidin-3-one o-methyloxime useful in methods of treating conditions related to the ot-r activity |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020186785A Division JP2021038236A (ja) | 2014-07-02 | 2020-11-09 | Ot−r活性に関する疾患を治療するための方法に有用な結晶質の(3z,5s)−5−(ヒドロキシメチル)−1−[(2’−メチル−1,1’−ビフェニル−4−イル)カルボニル]ピロリジン−3−オン о−メチルオキシム |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2017519015A true JP2017519015A (ja) | 2017-07-13 |
| JP2017519015A5 JP2017519015A5 (enExample) | 2018-07-05 |
Family
ID=53434312
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016573776A Pending JP2017519015A (ja) | 2014-07-02 | 2015-06-10 | Ot−r活性に関する疾患を治療するための方法に有用な結晶質の(3z,5s)−5−(ヒドロキシメチル)−1−[(2’−メチル−1,1’−ビフェニル−4−イル)カルボニル]ピロリジン−3−オン о−メチルオキシム |
| JP2020186785A Pending JP2021038236A (ja) | 2014-07-02 | 2020-11-09 | Ot−r活性に関する疾患を治療するための方法に有用な結晶質の(3z,5s)−5−(ヒドロキシメチル)−1−[(2’−メチル−1,1’−ビフェニル−4−イル)カルボニル]ピロリジン−3−オン о−メチルオキシム |
| JP2022184804A Pending JP2023018037A (ja) | 2014-07-02 | 2022-11-18 | Ot-r活性に関する疾患を治療するための方法に有用な結晶質の(3z,5s)-5-(ヒドロキシメチル)-1-[(2’-メチル-1,1’-ビフェニル-4-イル)カルボニル]ピロリジン-3-オン о-メチルオキシム |
| JP2024182585A Pending JP2025013885A (ja) | 2014-07-02 | 2024-10-18 | Ot-r活性に関する疾患を治療するための方法に有用な結晶質の(3z,5s)-5-(ヒドロキシメチル)-1-[(2’-メチル-1,1’-ビフェニル-4-イル)カルボニル]ピロリジン-3-オン о-メチルオキシム |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020186785A Pending JP2021038236A (ja) | 2014-07-02 | 2020-11-09 | Ot−r活性に関する疾患を治療するための方法に有用な結晶質の(3z,5s)−5−(ヒドロキシメチル)−1−[(2’−メチル−1,1’−ビフェニル−4−イル)カルボニル]ピロリジン−3−オン о−メチルオキシム |
| JP2022184804A Pending JP2023018037A (ja) | 2014-07-02 | 2022-11-18 | Ot-r活性に関する疾患を治療するための方法に有用な結晶質の(3z,5s)-5-(ヒドロキシメチル)-1-[(2’-メチル-1,1’-ビフェニル-4-イル)カルボニル]ピロリジン-3-オン о-メチルオキシム |
| JP2024182585A Pending JP2025013885A (ja) | 2014-07-02 | 2024-10-18 | Ot-r活性に関する疾患を治療するための方法に有用な結晶質の(3z,5s)-5-(ヒドロキシメチル)-1-[(2’-メチル-1,1’-ビフェニル-4-イル)カルボニル]ピロリジン-3-オン о-メチルオキシム |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US9718772B2 (enExample) |
| EP (2) | EP3753921A1 (enExample) |
| JP (4) | JP2017519015A (enExample) |
| KR (1) | KR102470283B1 (enExample) |
| CN (3) | CN106795110A (enExample) |
| AU (1) | AU2015283133B2 (enExample) |
| CA (1) | CA2953722C (enExample) |
| EA (2) | EA031353B1 (enExample) |
| ES (1) | ES2774789T3 (enExample) |
| IL (1) | IL249652B (enExample) |
| MX (1) | MX371068B (enExample) |
| UA (1) | UA122210C2 (enExample) |
| WO (1) | WO2016000920A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2021042153A (ja) * | 2019-09-10 | 2021-03-18 | Jfeケミカル株式会社 | パラターフェニルテトラカルボン酸およびパラターフェニルテトラカルボン酸二無水物の製造方法 |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2845850A1 (en) | 2013-09-10 | 2015-03-11 | ObsEva S.A. | Pyrrolidine derivatives as oxytocin/vasopressin V1a receptors antagonists |
| EP2886107A1 (en) | 2013-12-17 | 2015-06-24 | ObsEva S.A. | Oral formulations of pyrrolydine derivatives |
| UA122210C2 (uk) | 2014-07-02 | 2020-10-12 | Обсева С.А. | Кристалічний о-метилоксим (3z,5s)-5-(гідроксиметил)-1-[(2'-метил-1,1'-біфеніл-4-іл)карбоніл]піролідин-3-oну, корисний у способах лікування станів, пов'язаних з активністю ot-r |
| AU2017205254B2 (en) | 2016-01-04 | 2021-05-20 | Xoma (Us) Lcc | Alpha-amino esters of hydroxypropylthiazolidine carboxamide derivative and salt form, crystal polymorph thereof |
| WO2018015497A2 (en) | 2016-07-21 | 2018-01-25 | ObsEva S.A. | Oxytocin antagonist dosing regimens for promoting embryo implantation and preventing miscarriage |
| CN114667141A (zh) * | 2019-09-03 | 2022-06-24 | 奥布赛瓦股份公司 | 用于促进胚胎移植和预防流产的催产素拮抗剂给药方案 |
| WO2021160597A1 (en) | 2020-02-10 | 2021-08-19 | ObsEva S.A. | Biomarkers for oxytocin receptor antagonist therapy |
| EP4313061A4 (en) * | 2021-03-31 | 2025-03-05 | The Board of Trustees of the Leland Stanford Junior University | FORMULATIONS FOR PROLONGATION OF GESTATION AND FOR COMPLICATIONS OF MENSTRUATION OR GESTATION |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005533828A (ja) * | 2002-07-05 | 2005-11-10 | アプライド リサーチ システムズ エーアールエス ホールディング ナームロゼ フェンノートシャップ | オキシトシン拮抗物質としてのピロリジン誘導体 |
| JP6462030B2 (ja) * | 2013-09-10 | 2019-01-30 | オブセヴァ エス.エー. | オキシトシン/バソプレッシンV1aレセプターのアンタゴニストとしてのピロリジン誘導体を含有する医薬組成物 |
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| YU120988A (en) | 1988-06-23 | 1990-06-30 | Lek Tovarna Farmacevtskih | Process for preparing new dispersion pills of cimetidine |
| YU183988A (en) | 1988-09-30 | 1990-08-31 | Lek Tovarna Farmacevtskih | Process for preparing dispersion pills of dihydroergotoxine |
| JP2927532B2 (ja) | 1989-11-09 | 1999-07-28 | 塩野義製薬株式会社 | 含窒素異項環オキシーフェノキシ酢酸誘導体およびその除草剤としての用途 |
| US5889001A (en) | 1993-07-29 | 1999-03-30 | American Cyanamid Company | Tricyclic diazepine vasopressin antagonists and oxytocin antagonists |
| JP3534903B2 (ja) | 1995-06-09 | 2004-06-07 | 鐘淵化学工業株式会社 | 1−[3−クロロ−(2s)−メチルプロピオニル]−ピロリジン−(2s)−カルボン酸の製造方法 |
| GB9603699D0 (en) | 1996-02-21 | 1996-04-17 | Boots Co Plc | Therapeutic composition |
| US6696484B2 (en) | 1997-10-31 | 2004-02-24 | University Of Chicago Office Of Technology And Intellectual Property | Method and compositions for regulation of 5-alpha reductase activity |
| US6329418B1 (en) | 1998-04-14 | 2001-12-11 | The Procter & Gamble Company | Substituted pyrrolidine hydroxamate metalloprotease inhibitors |
| HK1046644B (en) | 1999-12-09 | 2006-11-10 | Reckitt Benckiser Healthcare (Uk) Limited | Compressed tablet composition comprising a nsaid |
| PT1268418E (pt) | 2000-03-27 | 2006-08-31 | Applied Research Systems | Derivados da pirrolidina farmacologicamente activos com inibidores bax |
| HRP20020705A2 (en) | 2000-03-27 | 2004-12-31 | Applied Research Systems | Pharmaceutically active pyrrolidine derivatives |
| TW536751B (en) | 2000-07-14 | 2003-06-11 | Nitto Denko Corp | Cleaning sheet, conveying member using the same, and substrate processing equipment cleaning method using them |
| DE60226431D1 (de) | 2001-03-20 | 2008-06-19 | Serono Lab | Pyrrolidinesterderivate mit oxytocinmodulierender wirkung |
| KR200245627Y1 (ko) * | 2001-05-15 | 2001-10-15 | 김병두 | 전기 가열부재가 부착된 냄비 |
| CA2449578C (en) | 2001-06-18 | 2011-12-13 | Applied Research Systems Ars Holding N.V. | Pyrrolidine oxadiazole- and thiadiazole derivatives |
| JP2003192582A (ja) | 2001-12-12 | 2003-07-09 | Merck Patent Gmbh | ナプロキセンナトリウムを含む速放性錠剤 |
| ATE449067T1 (de) | 2003-02-27 | 2009-12-15 | Merck Serono Sa | Pyrrolidin-derivate als oxytocin antagonisten |
| EA011026B1 (ru) | 2004-02-26 | 2008-12-30 | Лаборатуар Сероно Са | Способ получения пирролидиноксимов |
| GB2411355B (en) | 2004-02-27 | 2006-02-22 | Niche Generics Ltd | Pharmaceutical composition |
| MX2007014022A (es) | 2005-05-10 | 2008-02-07 | Ferring Int Ct Sa | Uso de antagonistas de oxitocina y/o vasopresina en la reproduccion asistida. |
| JP2008189732A (ja) | 2007-02-01 | 2008-08-21 | Fujifilm Corp | セルロースアシレート組成物、セルロースアシレートフィルム、光学補償シート、偏光板および液晶表示装置 |
| PL2572705T3 (pl) | 2007-10-01 | 2018-01-31 | Lesvi Laboratorios Sl | Tabletki ulegające rozpadowi w jamie ustnej |
| US9201077B2 (en) | 2009-07-27 | 2015-12-01 | Colorado State University Research Foundation | Direct enzyme immunoassay for measurement of serum progesterone levels |
| CA2892000A1 (en) | 2012-11-26 | 2014-05-30 | Piotr Pierzynski | Method and system for diagnosing uterine contraction levels using image analysis |
| EP2886107A1 (en) * | 2013-12-17 | 2015-06-24 | ObsEva S.A. | Oral formulations of pyrrolydine derivatives |
| UA122210C2 (uk) | 2014-07-02 | 2020-10-12 | Обсева С.А. | Кристалічний о-метилоксим (3z,5s)-5-(гідроксиметил)-1-[(2'-метил-1,1'-біфеніл-4-іл)карбоніл]піролідин-3-oну, корисний у способах лікування станів, пов'язаних з активністю ot-r |
| EP3501533B1 (en) | 2014-12-22 | 2025-07-09 | Ferring B.V. | Obe001 for use in the treatment in implantation and pregnancy in women undergoing assisted reproductive technologies |
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2015
- 2015-06-10 UA UAA201700678A patent/UA122210C2/uk unknown
- 2015-06-10 EA EA201790080A patent/EA031353B1/ru unknown
- 2015-06-10 MX MX2016016751A patent/MX371068B/es active IP Right Grant
- 2015-06-10 US US14/735,215 patent/US9718772B2/en active Active
- 2015-06-10 EA EA201891873A patent/EA201891873A1/ru unknown
- 2015-06-10 CA CA2953722A patent/CA2953722C/en active Active
- 2015-06-10 EP EP19204954.2A patent/EP3753921A1/en active Pending
- 2015-06-10 CN CN201580047177.XA patent/CN106795110A/zh active Pending
- 2015-06-10 WO PCT/EP2015/062881 patent/WO2016000920A1/en not_active Ceased
- 2015-06-10 CN CN202111228955.9A patent/CN114105850A/zh active Pending
- 2015-06-10 EP EP15730094.8A patent/EP3164384B1/en active Active
- 2015-06-10 JP JP2016573776A patent/JP2017519015A/ja active Pending
- 2015-06-10 AU AU2015283133A patent/AU2015283133B2/en active Active
- 2015-06-10 ES ES15730094T patent/ES2774789T3/es active Active
- 2015-06-10 CN CN202111229040.XA patent/CN114105851A/zh active Pending
- 2015-06-10 KR KR1020177001267A patent/KR102470283B1/ko active Active
-
2016
- 2016-12-19 IL IL249652A patent/IL249652B/en unknown
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2017
- 2017-05-25 US US15/604,816 patent/US10752583B2/en active Active
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2020
- 2020-11-09 JP JP2020186785A patent/JP2021038236A/ja active Pending
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2022
- 2022-11-18 JP JP2022184804A patent/JP2023018037A/ja active Pending
-
2024
- 2024-10-18 JP JP2024182585A patent/JP2025013885A/ja active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005533828A (ja) * | 2002-07-05 | 2005-11-10 | アプライド リサーチ システムズ エーアールエス ホールディング ナームロゼ フェンノートシャップ | オキシトシン拮抗物質としてのピロリジン誘導体 |
| JP6462030B2 (ja) * | 2013-09-10 | 2019-01-30 | オブセヴァ エス.エー. | オキシトシン/バソプレッシンV1aレセプターのアンタゴニストとしてのピロリジン誘導体を含有する医薬組成物 |
Non-Patent Citations (2)
| Title |
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| 社団法人 日本化学会, 実験化学講座1 基本操作I, vol. 第4版, JPN6018001753, 5 November 1990 (1990-11-05), pages 184 - 186, ISSN: 0003975180 * |
| 芦澤 一英、他, 医薬品の多形現象と晶析の科学, JPN7015003233, 20 September 2002 (2002-09-20), pages 305 - 317, ISSN: 0003975181 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2021042153A (ja) * | 2019-09-10 | 2021-03-18 | Jfeケミカル株式会社 | パラターフェニルテトラカルボン酸およびパラターフェニルテトラカルボン酸二無水物の製造方法 |
| JP7083793B2 (ja) | 2019-09-10 | 2022-06-13 | Jfeケミカル株式会社 | パラターフェニルテトラカルボン酸およびパラターフェニルテトラカルボン酸二無水物の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2015283133B2 (en) | 2019-05-16 |
| KR102470283B1 (ko) | 2022-11-23 |
| EA201891873A1 (ru) | 2019-04-30 |
| EP3164384B1 (en) | 2019-12-04 |
| ES2774789T3 (es) | 2020-07-22 |
| US9718772B2 (en) | 2017-08-01 |
| US10752583B2 (en) | 2020-08-25 |
| EP3753921A1 (en) | 2020-12-23 |
| WO2016000920A1 (en) | 2016-01-07 |
| CA2953722C (en) | 2022-09-13 |
| US20170320822A1 (en) | 2017-11-09 |
| EA201790080A1 (ru) | 2017-06-30 |
| CN106795110A (zh) | 2017-05-31 |
| IL249652B (en) | 2021-09-30 |
| CN114105850A (zh) | 2022-03-01 |
| MX2016016751A (es) | 2017-08-08 |
| US20160002160A1 (en) | 2016-01-07 |
| AU2015283133A1 (en) | 2017-02-16 |
| MX371068B (es) | 2020-01-15 |
| IL249652A0 (en) | 2017-02-28 |
| EP3164384A1 (en) | 2017-05-10 |
| UA122210C2 (uk) | 2020-10-12 |
| EA031353B1 (ru) | 2018-12-28 |
| CA2953722A1 (en) | 2016-01-07 |
| JP2023018037A (ja) | 2023-02-07 |
| CN114105851A (zh) | 2022-03-01 |
| KR20170023961A (ko) | 2017-03-06 |
| JP2025013885A (ja) | 2025-01-28 |
| JP2021038236A (ja) | 2021-03-11 |
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