ME02838B - 3,4-dihidroizokinolin-2(1h)-ilni spojevi - Google Patents
3,4-dihidroizokinolin-2(1h)-ilni spojeviInfo
- Publication number
- ME02838B ME02838B MEP-2017-221A MEP2017221A ME02838B ME 02838 B ME02838 B ME 02838B ME P2017221 A MEP2017221 A ME P2017221A ME 02838 B ME02838 B ME 02838B
- Authority
- ME
- Montenegro
- Prior art keywords
- compound according
- halogen
- crystalline form
- och
- alkoxy
- Prior art date
Links
- -1 3,4-dihydroisoquinoline-2 (1H) -yl COMPOUNDS Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 11
- 229910052736 halogen Inorganic materials 0.000 claims 8
- 150000002367 halogens Chemical class 0.000 claims 8
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- QBKZBAUOKUPKIJ-GOEBONIOSA-N 2-(2,6-dichlorophenyl)-1-[(1s,3r)-3-(hydroxymethyl)-5-(2-hydroxy-2-methylpropyl)-1-methyl-3,4-dihydro-1h-isoquinolin-2-yl]ethanone Chemical compound N1([C@H](C2=CC=CC(CC(C)(C)O)=C2C[C@@H]1CO)C)C(=O)CC1=C(Cl)C=CC=C1Cl QBKZBAUOKUPKIJ-GOEBONIOSA-N 0.000 claims 2
- XHCSBQBBGNQINS-DOTOQJQBSA-N 2-(2,6-dichlorophenyl)-1-[(1s,3r)-3-(hydroxymethyl)-5-(3-hydroxy-3-methylbutyl)-1-methyl-3,4-dihydro-1h-isoquinolin-2-yl]ethanone Chemical compound N1([C@H](C2=CC=CC(CCC(C)(C)O)=C2C[C@@H]1CO)C)C(=O)CC1=C(Cl)C=CC=C1Cl XHCSBQBBGNQINS-DOTOQJQBSA-N 0.000 claims 2
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 238000000634 powder X-ray diffraction Methods 0.000 claims 2
- 230000005855 radiation Effects 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
- C07D217/16—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals substituted by oxygen atoms
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychology (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Epidemiology (AREA)
- Plural Heterocyclic Compounds (AREA)
Claims (16)
1. Spoj formule , naznačen time što n je 0, 1 ili 2; R1 je halogen; R2 je halogen, H, CN, C1-C3 alkoksi ili C1-C3 alkil; i R3 je H, halogen, C1-C3 alkoksi ili C1-C3 alkil.
2. Spoj u skladu s patentnim zahtjevom 1, naznačen time što ima formulu , gdje n je 0, 1 ili 2; R1 je halogen; R2 je halogen, H, CN, C1-C3 alkoksi ili C1-C3 alkil; i R3 je H, halogen, C1-C3 alkoksi ili C1-C3 alkil.
3. Spoj u skladu s bilo patentnim zahtjevom 1 ili 2, naznačen time što n je 0, 1 ili 2; R1 je halogen; R2 je halogen; i R3 je vodik ili C1-C3 alkoksi.
4. Spoj u skladu s bilo patentnim zahtjevom 1 ili 2, naznačen time što n je 0, 1 ili 2; R1 je Cl, F ili Br; R2 je Cl, OCH3, H, F, CN ili CH3; i R3 je OCH3, H, CH2CH3, Cl, OCH(CH3)2, OCH2CH3, F, CH(CH3)2 ili CH3.
5. Spoj u skladu s bilo kojim od patentnih zahtjeva 1, 2 ili 3, naznačen time što n je 0 ili 2; R1 je Cl; R2 je Cl ili F; i R3 je H ili OCH3.
6. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je 2-(2,6-diklorfenil)-1-[(1S,3R)-3-(hidroksimetil)-5-(3-hidroksi-3-metilbutil)-1-metil-3,4-dihidroizokinolin-2(1H)-il]etanon.
7. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je 2-(2,6-diklorfenil)-1-((1S,3R)-5-(2-hidroksi-2-metilpropil)-3-(hidroksimetil)-1-metil-3,4-dihidroizokinolin-2(1H)-il)etan-1-on.
8. Pripravak, naznačen time što sadrži 2-(2,6-diklorfenil)-1-[(1S,3R)-3-(hidroksimetil)-5-(3-hidroksi-3-metilbutil)-1-metil-3,4-dihidroizokinolin-2(1H)-il]etanon i 4-hidroksibenzojevu kiselinu.
9. Sukristalni oblik, naznačen time što je sukristalni oblik pripravka u skladu s patentnim zahtjevom 8.
10. Sukristalni oblik pripravka u skladu s patentnim zahtjevom 9, naznačen time što ima uzorak difrakcije rendgenskih zraka na prahu, uz upotrebu CuKα zračenja, s difrakcijskim maksimumom pod difrakcijskim kutom 2θ od 18,2°, u kombinaciji s jednim ili više maksimuma koje se bira iz skupine koju čine 16,0°, 25,4°, te 7,0°; uz toleranciju za difrakcijske kutove od 0,2°.
11. Sukristalni oblik, naznačen time što je sukristalni oblik 2-(2,6-diklorfenil)-1-((1S,3R)-5-(2-hidroksi-2-metilpropil)-3-(hidroksimetil)-1-metil-3,4-dihidroizokinolin-2(1H)-il)etan-1-ona i 4-hidroksibenzojeve kiseline.
12. Sukristalni oblik u skladu s patentnim zahtjevom 11, naznačen time što ima uzorak difrakcije rendgenskih zraka na prahu, uz upotrebu CuKα zračenja, s difrakcijskim maksimumom pod difrakcijskim kutom 2θ od 7,0°, u kombinaciji s jednim ili više maksimuma koje se bira iz skupine koju čine 18,8°, 16,1°, te 19.3°; uz toleranciju za difrakcijske kutove od 0,2°.
13. Farmaceutski pripravak, naznačen time što sadrži spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 7, kao i farmaceutski prihvatljivu podlogu, razrjeđivač ili pomoćnu tvar.
14. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 7, naznačen time što je namijenjen upotrebi u terapiji.
15. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 7, naznačen time što je namijenjen upotrebi u liječenju Parkinsonove bolesti.
16. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 7, naznačen time što je namijenjen upotrebi u liječenju shizofrenije.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361828740P | 2013-05-30 | 2013-05-30 | |
| US201361905329P | 2013-11-18 | 2013-11-18 | |
| EP14732756.3A EP3004061B8 (en) | 2013-05-30 | 2014-05-27 | 3,4-dihydroisoquinolin-2(1h)-yl compounds |
| PCT/US2014/039494 WO2014193781A1 (en) | 2013-05-30 | 2014-05-27 | 3,4-dihydroisoquinolin-2(1h)-yl compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ME02838B true ME02838B (me) | 2018-01-20 |
Family
ID=50983199
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MEP-2017-221A ME02838B (me) | 2013-05-30 | 2014-05-27 | 3,4-dihidroizokinolin-2(1h)-ilni spojevi |
Country Status (37)
| Country | Link |
|---|---|
| US (1) | US8962654B2 (me) |
| EP (1) | EP3004061B8 (me) |
| JP (2) | JP6130590B2 (me) |
| KR (1) | KR101808933B1 (me) |
| CN (1) | CN105228985B (me) |
| AP (1) | AP2015008867A0 (me) |
| AU (2) | AU2014274435B2 (me) |
| BR (1) | BR112015029090B1 (me) |
| CA (1) | CA2912849C (me) |
| CL (1) | CL2015003444A1 (me) |
| CR (1) | CR20150622A (me) |
| CY (1) | CY1119361T1 (me) |
| DK (1) | DK3004061T3 (me) |
| DO (1) | DOP2015000289A (me) |
| EA (1) | EA029220B1 (me) |
| ES (1) | ES2647086T3 (me) |
| GT (1) | GT201500334A (me) |
| HR (1) | HRP20171696T1 (me) |
| HU (1) | HUE034607T2 (me) |
| JO (1) | JO3316B1 (me) |
| LT (1) | LT3004061T (me) |
| ME (1) | ME02838B (me) |
| MX (1) | MX373843B (me) |
| MY (1) | MY180751A (me) |
| NZ (1) | NZ713809A (me) |
| PE (1) | PE20152032A1 (me) |
| PH (1) | PH12015502658B1 (me) |
| PL (1) | PL3004061T3 (me) |
| PT (1) | PT3004061T (me) |
| RS (1) | RS56294B1 (me) |
| SG (1) | SG11201509310QA (me) |
| SI (1) | SI3004061T1 (me) |
| TN (1) | TN2015000514A1 (me) |
| TW (2) | TWI691489B (me) |
| UA (1) | UA118759C2 (me) |
| WO (1) | WO2014193781A1 (me) |
| ZA (1) | ZA201508213B (me) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2754398T3 (es) | 2009-11-27 | 2020-04-17 | Genzyme Corp | Eliglustat (Genz 112638) como inhibidor de glucosilceramida-sintasa para uso en un método de tratamiento de la enfermedad de fabry o de gaucher, comprendiendo el método ajustar la dosis terapéutica individual al metabolismo P-450 del paciente |
| JO3316B1 (ar) * | 2013-05-30 | 2019-03-13 | Lilly Co Eli | مركبات 3، 4-داي هيدرو أيزو كوينولين -2(1h)-يل |
| AR106332A1 (es) * | 2015-10-23 | 2018-01-03 | Lilly Co Eli | Forma cristalina de 2-(2,6-diclorofenil)-1-[(1s,3r)-3-(hidroximetil)-5-(3-hidroxi-3-metilbutil)-1-metil-3,4-dihidroisoquinolin-2(1h)-il]etanona |
| EA036137B1 (ru) | 2016-04-13 | 2020-10-02 | Юсб Байофарма Спрл | Производные тетрагидроизохинолина |
| IL309069A (en) | 2017-02-21 | 2024-02-01 | Univ Emory | CXCR4 cytokine receptor modulators and related uses |
| EP3418270A1 (en) | 2017-06-19 | 2018-12-26 | Universidad Complutense De Madrid | Novel biphenylsulfoximines as allosteric modulators of the dopamine d1 receptor |
| DK3717025T3 (da) * | 2017-12-01 | 2021-11-22 | UCB Biopharma SRL | Billeddannende midler |
| TWI725408B (zh) * | 2018-04-20 | 2021-04-21 | 美商美國禮來大藥廠 | 多巴胺d1受體正向異位調節劑 |
| JP2022514659A (ja) | 2018-12-18 | 2022-02-14 | イーライ リリー アンド カンパニー | ドーパミン作動性ｃｎｓ障害の治療におけるｌｙ３１５４２０７の使用のための用量レジメン |
| TWI843678B (zh) * | 2019-06-18 | 2024-05-21 | 美商美國禮來大藥廠 | 用於製備2-(2,6-二氯苯基)-1-[(1s,3r)-3-(羥甲基)-5-(3-羥基-3-甲基丁基)-1-甲基-3,4-二氫異喹啉-2(1h)-基]乙烯酮之方法及中間物 |
| EP3993795A1 (en) * | 2019-07-01 | 2022-05-11 | UCB Biopharma SRL | A substituted tetrahydroisoquinoline derivative as a d1 positive allosteric modulator |
| WO2021001288A1 (en) * | 2019-07-01 | 2021-01-07 | UCB Biopharma SRL | A substituted tetrahydroisoquinoline derivative as a d1 positive allosteric modulator |
| SI4200280T1 (sl) * | 2020-10-07 | 2024-04-30 | Eli Lilly And Company | Derivati fenil-3,4-dihidroizokvinolin-2(1H)-il-etan-1-ona kot pozitivni alosterični modulatorji dopamin D1 receptorja |
| CA3198635A1 (en) * | 2020-12-03 | 2022-06-09 | UCB Biopharma SRL | Octahydroisoquinolinyl derivatives |
| WO2022129303A1 (en) * | 2020-12-18 | 2022-06-23 | UCB Biopharma SRL | Dihydroisoquinolinyl derivatives |
| CN116601161A (zh) * | 2020-12-18 | 2023-08-15 | Ucb生物制药有限责任公司 | 2-(3,5-二氯-1-甲基-吲唑-4-基)-1-[(1s,3r)-3-(羟基甲基)-5-(1-羟基-1-甲基-乙基)-1-甲基-3,4-二氢-1h-异喹啉-2-基]乙酮的前药 |
| KR20230121867A (ko) * | 2020-12-18 | 2023-08-21 | 유씨비 바이오파마 에스알엘 | 무정형 고체 분산체 |
| CA3202993A1 (en) | 2020-12-18 | 2022-06-23 | UCB Biopharma SRL | A substituted tetrahydroisoquinoline derivative as a d1 positive allosteric modulator |
| US20240299375A1 (en) | 2021-03-08 | 2024-09-12 | Eli Lilly And Company | Use of mevidalen and other d1 positive allosteric modulators in the treatment of hallucinations and dementia-related psychosis |
| KR20230154968A (ko) * | 2021-03-09 | 2023-11-09 | 일라이 릴리 앤드 캄파니 | 파킨슨병 진행을 늦추기 위한 메비달렌 및 다른 d1 양성 알로스테릭 조절제의 용도 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0330360B1 (en) | 1988-02-19 | 1993-12-01 | SmithKline Beecham Farmaceutici S.p.A. | 1,2,3,4-Tetrahydroisoquinolines, processes for their preparation, and their use as kappa-receptor agonists |
| US5246943A (en) * | 1992-05-19 | 1993-09-21 | Warner-Lambert Company | Substituted 1,2,3,4-tetahydroisoquinolines with angiotensin II receptor antagonist properties |
| US5236934A (en) * | 1992-08-26 | 1993-08-17 | E. I. Du Pont De Nemours And Company | 1,2,3,4-tetrahydroisoquinolines useful in the treatment of CNS disorders |
| US5932590A (en) | 1996-12-05 | 1999-08-03 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| PL342843A1 (en) | 1998-02-18 | 2001-07-16 | Neurosearch As | Novel compounds and their use as positive ampa receptor modulators |
| ATE310728T1 (de) | 2000-05-11 | 2005-12-15 | Bristol Myers Squibb Co | Tetrahydroisochinolin-analoga als wachstumshormon-sekretagoga |
| US7601739B2 (en) | 2003-08-08 | 2009-10-13 | Virgina Commonwealth University | Compounds having antiestrogenic and tissue selective estrogenic properties, and compounds with anti-androgenic properties for treatment of prostate cancer and androgen receptor dependent diseases |
| US7541466B2 (en) | 2003-12-23 | 2009-06-02 | Genzyme Corporation | Tetrahydroisoquinoline derivatives for treating protein trafficking diseases |
| BRPI0808525A2 (pt) * | 2007-03-01 | 2014-08-19 | Janssen Pharmaceutica Nv | Compostos de tetraidroisoquinolina como moduladors do receptor de histamina h3 |
| US20120252853A1 (en) * | 2011-04-01 | 2012-10-04 | H. Lundbeck A/S | Positive allosteric modulators of nicotinic acetylcholine receptor |
| ES2624379T3 (es) | 2011-12-21 | 2017-07-14 | Idorsia Pharmaceuticals Ltd | Derivados de heterociclilo y su uso como moduladores del receptor de prostaglandina D2 |
| JO3316B1 (ar) * | 2013-05-30 | 2019-03-13 | Lilly Co Eli | مركبات 3، 4-داي هيدرو أيزو كوينولين -2(1h)-يل |
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2014
- 2014-05-15 JO JOP/2014/0163A patent/JO3316B1/ar active
- 2014-05-16 TW TW108104751A patent/TWI691489B/zh active
- 2014-05-16 TW TW103117402A patent/TWI691488B/zh active
- 2014-05-27 UA UAA201511029A patent/UA118759C2/uk unknown
- 2014-05-27 HU HUE14732756A patent/HUE034607T2/en unknown
- 2014-05-27 AP AP2015008867A patent/AP2015008867A0/xx unknown
- 2014-05-27 JP JP2016516713A patent/JP6130590B2/ja active Active
- 2014-05-27 CN CN201480031030.7A patent/CN105228985B/zh active Active
- 2014-05-27 LT LTEP14732756.3T patent/LT3004061T/lt unknown
- 2014-05-27 EA EA201592082A patent/EA029220B1/ru not_active IP Right Cessation
- 2014-05-27 TN TN2015000514A patent/TN2015000514A1/en unknown
- 2014-05-27 MX MX2015016495A patent/MX373843B/es active IP Right Grant
- 2014-05-27 MY MYPI2015704341A patent/MY180751A/en unknown
- 2014-05-27 AU AU2014274435A patent/AU2014274435B2/en active Active
- 2014-05-27 SG SG11201509310QA patent/SG11201509310QA/en unknown
- 2014-05-27 PT PT147327563T patent/PT3004061T/pt unknown
- 2014-05-27 KR KR1020157033616A patent/KR101808933B1/ko active Active
- 2014-05-27 WO PCT/US2014/039494 patent/WO2014193781A1/en not_active Ceased
- 2014-05-27 EP EP14732756.3A patent/EP3004061B8/en active Active
- 2014-05-27 ES ES14732756.3T patent/ES2647086T3/es active Active
- 2014-05-27 SI SI201430377T patent/SI3004061T1/sl unknown
- 2014-05-27 HR HRP20171696TT patent/HRP20171696T1/hr unknown
- 2014-05-27 CA CA2912849A patent/CA2912849C/en active Active
- 2014-05-27 ME MEP-2017-221A patent/ME02838B/me unknown
- 2014-05-27 NZ NZ71380914A patent/NZ713809A/en unknown
- 2014-05-27 US US14/287,239 patent/US8962654B2/en active Active
- 2014-05-27 PL PL14732756T patent/PL3004061T3/pl unknown
- 2014-05-27 PE PE2015002534A patent/PE20152032A1/es unknown
- 2014-05-27 RS RS20170896A patent/RS56294B1/sr unknown
- 2014-05-27 DK DK14732756.3T patent/DK3004061T3/en active
- 2014-05-27 BR BR112015029090-6A patent/BR112015029090B1/pt active IP Right Grant
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2015
- 2015-11-06 ZA ZA2015/08213A patent/ZA201508213B/en unknown
- 2015-11-23 CR CR20150622A patent/CR20150622A/es unknown
- 2015-11-24 CL CL2015003444A patent/CL2015003444A1/es unknown
- 2015-11-26 GT GT201500334A patent/GT201500334A/es unknown
- 2015-11-27 DO DO2015000289A patent/DOP2015000289A/es unknown
- 2015-11-27 PH PH12015502658A patent/PH12015502658B1/en unknown
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2016
- 2016-10-07 AU AU2016238934A patent/AU2016238934B2/en active Active
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2017
- 2017-04-13 JP JP2017079775A patent/JP6387433B2/ja active Active
- 2017-10-05 CY CY20171101039T patent/CY1119361T1/el unknown
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