HRP20220665T1 - Natrijeve soli 5-brom-2-(alfa-hidroksipentil)benzojeve kiseline u različitim kristalnim oblicima i postupak njihove pripreme - Google Patents
Natrijeve soli 5-brom-2-(alfa-hidroksipentil)benzojeve kiseline u različitim kristalnim oblicima i postupak njihove pripreme Download PDFInfo
- Publication number
- HRP20220665T1 HRP20220665T1 HRP20220665TT HRP20220665T HRP20220665T1 HR P20220665 T1 HRP20220665 T1 HR P20220665T1 HR P20220665T T HRP20220665T T HR P20220665TT HR P20220665 T HRP20220665 T HR P20220665T HR P20220665 T1 HRP20220665 T1 HR P20220665T1
- Authority
- HR
- Croatia
- Prior art keywords
- bromo
- hydroxypentyl
- benzoic acid
- compound according
- sodium salt
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims 5
- 239000013078 crystal Substances 0.000 title 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 15
- HZEOKIXKYINUKT-UHFFFAOYSA-N 5-bromo-2-(1-hydroxypentyl)benzoic acid Chemical compound CCCCC(O)C1=CC=C(Br)C=C1C(O)=O HZEOKIXKYINUKT-UHFFFAOYSA-N 0.000 claims 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 9
- 238000000034 method Methods 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 6
- 159000000000 sodium salts Chemical class 0.000 claims 6
- 239000007787 solid Substances 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 4
- BFZOBNLAWCOYMD-UHFFFAOYSA-N 6-bromo-3-butyl-3h-2-benzofuran-1-one Chemical compound BrC1=CC=C2C(CCCC)OC(=O)C2=C1 BFZOBNLAWCOYMD-UHFFFAOYSA-N 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 3
- 238000000634 powder X-ray diffraction Methods 0.000 claims 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 3
- 239000011541 reaction mixture Substances 0.000 claims 2
- 206010048962 Brain oedema Diseases 0.000 claims 1
- 208000006752 brain edema Diseases 0.000 claims 1
- 210000005013 brain tissue Anatomy 0.000 claims 1
- 210000001627 cerebral artery Anatomy 0.000 claims 1
- 206010008118 cerebral infarction Diseases 0.000 claims 1
- -1 compound sodium salt Chemical class 0.000 claims 1
- 230000008020 evaporation Effects 0.000 claims 1
- 238000001704 evaporation Methods 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 208000037816 tissue injury Diseases 0.000 claims 1
- 238000002604 ultrasonography Methods 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/68—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings containing halogen
- C07C63/70—Monocarboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
- C07C65/03—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Crystallography & Structural Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (12)
1. Spoj natrijeva sol 5-brom-2-(α-hidroksipentil)benzojeve kiseline.
2. Spoj prema patentnom zahtjevu 1, naznačen time što je u amorfnom obliku.
3. Spoj prema patentnom zahtjevu 2, naznačen time što se priprema sljedećim postupkom: 6-brom-3-butil-1(3H)-izobenzofuranon i natrijev hidroksid se važu i stavljaju u kristalizator, u koji se dodaju tetrahidrofuran i voda, zatim se smjesa otapa i reagira u vodenoj kupelji na 60°C; nakon završetka reakcije, reakcijska smjesa se destilira pod sniženim tlakom kako bi se uklonila sva otapala da se dobije amorfna natrijeva sol 5-brom-2-(α- hidroksipentil)benzojeve kiseline, čiji XRPD uzorak nema očiti vrh difrakcije.
4. Spoj prema patentnom zahtjevu 1 u kristalnom obliku A, naznačen time što ima XRPD uzorak s vrhovima difrakcije na vrijednostima 2θ od 5.60, 16.46, 16.78, 18.77, 21.45, 32.28, 33.30, 33.49, 34.12, 36.14, 36.61, 37.87, 40.24, 41.32, 43.76, 44.92, 45.18, 47.23, 55.12, 56.73, 57.12, 62.78, pri čemu je raspon pogreške vrijednosti 2θ ±0.2.
5. Spoj prema patentnom zahtjevu 1 u kristalnom obliku B, naznačen time što ima XRPD uzorak s vrhovima difrakcije na vrijednostima 2θ od 5.72, 6.69, 9.93, 11.09, 11.84, 14.55, 16.42, 17.27, 17.80, 18.28, 19.86, 20.98, 22.21, 23.43, 23.88, pri čemu je raspon pogreške vrijednosti 2θ ±0.2.
6. Postupak za pripremu amorfne natrijeve soli 5-brom-2-(α-hidroksipentil) benzojeve kiseline prema patentnom zahtjevu 3, naznačen time što se 6-brom-3-butil-1(3H)-izobenzofuranon i natrijev hidroksid važu i stavljaju se u kristalizator, zatim se dodaju tetrahidrofuran i voda, zatim se smjesa otapa i reagira u vodenoj kupelji na 60°C; nakon završetka reakcije, reakcijska smjesa se destilira pod sniženim tlakom kako bi se uklonila sva otapala kako bi se dobila amorfna natrijeva sol 5-brom-2-(α-hidroksipentil)benzojeve kiseline.
7. Postupak za pripremu kristalnog oblika A natrijeve soli 5-brom-2-(α-hidroksipentil)benzojeve kiseline prema patentnom zahtjevu 4, naznačen time što se amorfna 5-brom-2-(α-hidroksipentil) benzojeva kiselina važe, zatim se dodaje otopina NaOH u metanolu, otapa se pod ultrazvukom, a zatim se otapalo polako isparava; nakon što se krute tvari istalože, krute tvari se suše u vakuumu.
8. Postupak za pripremu kristalnog oblika B natrijeve soli 5-brom-2-(α-hidroksipentil)benzojeve kiseline prema patentnom zahtjevu 5, naznačen time što se amorfna 5-brom-2-(α-hidroksipentil)benzojeva kiselina važe, zatim se dodaje tetrahidrofuran radi otapanja, a zatim se otopina miješa na sobnoj temperaturi; vodena otopina natrijevog hidroksida polagano se dodaje u kapima gore navedenoj otopini; nakon uparavanja otapala, dobivene su krute tvari, te se suše u vakuumu.
9. Postupak za pripremu kristalnog oblika B natrijeve soli 5-brom-2-(α-hidroksipentil)benzojeve kiseline prema patentnom zahtjevu 5, naznačen time što se važu 6-brom-3-butil-1(3H)-izobenzofuranon i natrijev hidroksid i stavljaju u tikvicu; u tikvicu se dodaje metanol, dobivena smjesa se zagrijava pod refluksom tako da reagira, a zatim se metanol isparava; dodaje se etil acetat, dobivena smjesa se protrese i neotopljene krute tvari se odfiltriraju; etil acetat se isparava kako bi se dobio kruti spoj, kojemu se dodaje bezvodni dietil eter da se otopi, a dobivena otopina se ostavlja stajati preko noći, te se zatim filtrira.
10. Spoj prema bilo kojem od patentnih zahtjeva 1 do 5, naznačen time što se koristi u postupku smanjenja ozljede moždanog tkiva uzrokovane opstrukcijom cerebralnih arterija.
11. Spoj prema bilo kojem od patentnih zahtjeva 1 do 5, naznačen time što se koristi u postupku smanjenja volumena infarkta mozga.
12. Spoj prema bilo kojem od patentnih zahtjeva 1 do 5, naznačen time što se koristi u postupku smanjenja volumena edema mozga.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201310299084 | 2013-07-17 | ||
CN201410313214.4A CN104086399B (zh) | 2013-07-17 | 2014-07-03 | 5-溴-2-(α-羟基戊基)苯甲酸钠盐的不同晶型及其制备方法 |
PCT/CN2014/081954 WO2015007181A1 (zh) | 2013-07-17 | 2014-07-10 | 5-溴-2-(α-羟基戊基)苯甲酸钠盐的不同晶型及其制备方法 |
EP14826150.6A EP3023410B1 (en) | 2013-07-17 | 2014-07-10 | 5-BROMINE-2-(alpha-HYDROXYPENTYL)BENZOIC ACID SODIUM SALTS IN DIFFERENT CRYSTAL FORMS, AND PREPARATION METHOD THEREOF |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20220665T1 true HRP20220665T1 (hr) | 2022-06-24 |
Family
ID=51634190
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HRP20220665TT HRP20220665T1 (hr) | 2013-07-17 | 2014-07-10 | Natrijeve soli 5-brom-2-(alfa-hidroksipentil)benzojeve kiseline u različitim kristalnim oblicima i postupak njihove pripreme |
Country Status (16)
Country | Link |
---|---|
US (4) | US9902682B2 (hr) |
EP (1) | EP3023410B1 (hr) |
JP (1) | JP6483674B2 (hr) |
KR (2) | KR102279367B1 (hr) |
CN (2) | CN104086399B (hr) |
DK (1) | DK3023410T3 (hr) |
ES (1) | ES2913338T3 (hr) |
HR (1) | HRP20220665T1 (hr) |
HU (1) | HUE058690T2 (hr) |
LT (1) | LT3023410T (hr) |
PL (1) | PL3023410T3 (hr) |
PT (1) | PT3023410T (hr) |
RS (1) | RS63249B1 (hr) |
RU (2) | RU2643802C2 (hr) |
SI (1) | SI3023410T1 (hr) |
WO (1) | WO2015007181A1 (hr) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104086399B (zh) * | 2013-07-17 | 2016-08-24 | 浙江奥翔药业股份有限公司 | 5-溴-2-(α-羟基戊基)苯甲酸钠盐的不同晶型及其制备方法 |
WO2018126897A1 (zh) * | 2017-01-06 | 2018-07-12 | 郑州大学 | 5-溴-2-(α-羟基戊基)苯甲酸钠在治疗心血管疾病药物中的应用 |
WO2019179346A1 (zh) * | 2018-03-19 | 2019-09-26 | 河南真实生物科技有限公司 | 苯甲酸类化合物及其制备方法和应用 |
CN108715579B (zh) | 2018-05-17 | 2020-03-24 | 四川大学 | 一种2-(α羟基戊基)苯甲酸的有机胺酯衍生物药物 |
CN109223749A (zh) * | 2018-11-14 | 2019-01-18 | 郑州大学 | 5- 溴-2-(α- 羟基戊基)苯甲酸钠盐在治疗心肌肥厚和心力衰竭中的药物用途 |
CN111943898A (zh) * | 2019-05-17 | 2020-11-17 | 浙江大学 | 苯联四氮唑类衍生物、制备、含其的药物组合物及其应用 |
US20230144023A1 (en) | 2020-03-20 | 2023-05-11 | Cspc Nbp Pharmaceutical Co., Ltd | Use of butylphthalide and derivative thereof |
US20230398087A1 (en) * | 2020-10-30 | 2023-12-14 | Zhejiang Ausun Pharmaceutical Co., Ltd. | Application of bzp in treatment of ischemic cardiovascular and cerebral vascular diseases |
CN112457265A (zh) * | 2020-11-06 | 2021-03-09 | 浙江大学 | 四氮唑类衍生物、制备、含其的药物组合物及其应用 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
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CN1243541C (zh) | 2002-05-09 | 2006-03-01 | 中国医学科学院药物研究所 | 2-(α-羟基戊基)苯甲酸盐及其制法和用途 |
RU2305092C2 (ru) * | 2002-05-09 | 2007-08-27 | Инститьют Оф Материя Медика, Чайниз Экедеми Оф Медикал Сайенсез | НОВЫЕ 2-(α-ГИДРОКСИПЕНТИЛ)БЕНЗОАТЫ, ИХ ПОЛУЧЕНИЕ И ПРИМЕНЕНИЕ |
CN100422133C (zh) * | 2003-09-01 | 2008-10-01 | 北京天衡药物研究院 | 2-(α-羟基戊基)苯甲酸盐及其制法和用途 |
CN100540523C (zh) * | 2004-06-17 | 2009-09-16 | 北京天衡药物研究院 | L-2-(α-羟基戊基)苯甲酸盐及其制法和用途 |
CN101054346A (zh) * | 2006-04-13 | 2007-10-17 | 温建波 | 一组新化合物及其组合物的制备方法和用途 |
CN100554259C (zh) | 2007-04-12 | 2009-10-28 | 郑州大学 | 2-苯并[c]呋喃酮化合物及其应用 |
CN101402565B (zh) * | 2008-11-14 | 2012-07-04 | 郑州大学 | 卤代2-(a-羟基戊基)苯甲酸盐及其制法和用途 |
CN103113210A (zh) * | 2013-02-19 | 2013-05-22 | 石药集团中奇制药技术(石家庄)有限公司 | 羟戊基苯甲酸钾晶体及其制备方法 |
CN104086399B (zh) * | 2013-07-17 | 2016-08-24 | 浙江奥翔药业股份有限公司 | 5-溴-2-(α-羟基戊基)苯甲酸钠盐的不同晶型及其制备方法 |
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2014
- 2014-07-03 CN CN201410313214.4A patent/CN104086399B/zh active Active
- 2014-07-10 LT LTEPPCT/CN2014/081954T patent/LT3023410T/lt unknown
- 2014-07-10 CN CN201480040408.XA patent/CN105517988B/zh active Active
- 2014-07-10 ES ES14826150T patent/ES2913338T3/es active Active
- 2014-07-10 RS RS20220486A patent/RS63249B1/sr unknown
- 2014-07-10 KR KR1020217008672A patent/KR102279367B1/ko active IP Right Grant
- 2014-07-10 SI SI201431955T patent/SI3023410T1/sl unknown
- 2014-07-10 KR KR1020167003719A patent/KR102279371B1/ko active IP Right Grant
- 2014-07-10 PT PT148261506T patent/PT3023410T/pt unknown
- 2014-07-10 HU HUE14826150A patent/HUE058690T2/hu unknown
- 2014-07-10 EP EP14826150.6A patent/EP3023410B1/en active Active
- 2014-07-10 WO PCT/CN2014/081954 patent/WO2015007181A1/zh active Application Filing
- 2014-07-10 HR HRP20220665TT patent/HRP20220665T1/hr unknown
- 2014-07-10 RU RU2016101132A patent/RU2643802C2/ru active
- 2014-07-10 US US14/905,199 patent/US9902682B2/en active Active
- 2014-07-10 JP JP2016526427A patent/JP6483674B2/ja active Active
- 2014-07-10 RU RU2018102357A patent/RU2738374C1/ru active
- 2014-07-10 DK DK14826150.6T patent/DK3023410T3/da active
- 2014-07-10 PL PL14826150T patent/PL3023410T3/pl unknown
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2017
- 2017-07-26 US US15/660,395 patent/US10377693B2/en active Active
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2019
- 2019-02-28 US US16/288,863 patent/US11148991B2/en active Active
- 2019-06-26 US US16/452,905 patent/US10604471B2/en active Active
Also Published As
Publication number | Publication date |
---|---|
US20160168069A1 (en) | 2016-06-16 |
KR102279371B1 (ko) | 2021-07-20 |
US20190315673A1 (en) | 2019-10-17 |
JP2016528210A (ja) | 2016-09-15 |
EP3023410B1 (en) | 2022-02-23 |
EP3023410A4 (en) | 2017-02-08 |
CN104086399A (zh) | 2014-10-08 |
SI3023410T1 (sl) | 2022-06-30 |
US9902682B2 (en) | 2018-02-27 |
KR20210035336A (ko) | 2021-03-31 |
RU2643802C2 (ru) | 2018-02-06 |
US10604471B2 (en) | 2020-03-31 |
US11148991B2 (en) | 2021-10-19 |
CN105517988A (zh) | 2016-04-20 |
JP6483674B2 (ja) | 2019-03-13 |
HUE058690T2 (hu) | 2022-09-28 |
DK3023410T3 (da) | 2022-05-23 |
PL3023410T3 (pl) | 2022-06-06 |
WO2015007181A1 (zh) | 2015-01-22 |
KR102279367B1 (ko) | 2021-07-20 |
CN104086399B (zh) | 2016-08-24 |
ES2913338T3 (es) | 2022-06-01 |
PT3023410T (pt) | 2022-06-28 |
US20180127349A1 (en) | 2018-05-10 |
LT3023410T (lt) | 2022-09-12 |
CN105517988B (zh) | 2017-04-12 |
US20190194116A1 (en) | 2019-06-27 |
RU2016101132A (ru) | 2017-08-22 |
KR20160031004A (ko) | 2016-03-21 |
US10377693B2 (en) | 2019-08-13 |
EP3023410A1 (en) | 2016-05-25 |
RS63249B1 (sr) | 2022-06-30 |
RU2738374C1 (ru) | 2020-12-11 |
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