HRP20171649T1 - 4-supstituirani spojevi 3-fenilsulfanilmetilbiciklo[3.1.0]heksana kao antagonisti mglur 2/3 - Google Patents
4-supstituirani spojevi 3-fenilsulfanilmetilbiciklo[3.1.0]heksana kao antagonisti mglur 2/3 Download PDFInfo
- Publication number
- HRP20171649T1 HRP20171649T1 HRP20171649TT HRP20171649T HRP20171649T1 HR P20171649 T1 HRP20171649 T1 HR P20171649T1 HR P20171649T T HRP20171649T T HR P20171649TT HR P20171649 T HRP20171649 T HR P20171649T HR P20171649 T1 HRP20171649 T1 HR P20171649T1
- Authority
- HR
- Croatia
- Prior art keywords
- compound according
- pharmaceutically acceptable
- acceptable salt
- methyl
- amino
- Prior art date
Links
- -1 4-substituted-3-phenylsulfanylmethyl-bicyclo[3.1.0]hexane compounds Chemical class 0.000 title claims 4
- 229940127592 mGluR2/3 antagonist Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 208000020401 Depressive disease Diseases 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- 229940126570 serotonin reuptake inhibitor Drugs 0.000 claims 2
- 239000003772 serotonin uptake inhibitor Substances 0.000 claims 2
- PVCLSZDVATUGHR-XJDZXMJWSA-N (1s,2r,3s,4s,5r,6r)-2-amino-3-[(3,4-difluorophenyl)sulfanylmethyl]-4-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylic acid Chemical compound C([C@@H]1[C@@H](O)[C@@H]2[C@@H]([C@H]2C(O)=O)[C@]1(N)C(O)=O)SC1=CC=C(F)C(F)=C1 PVCLSZDVATUGHR-XJDZXMJWSA-N 0.000 claims 1
- GTHAIOYBHQWJIR-XJDZXMJWSA-N (1s,2r,3s,4s,5r,6r)-2-amino-3-[(3-chloro-4-fluorophenyl)sulfanylmethyl]-4-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylic acid Chemical compound C([C@@H]1[C@@H](O)[C@@H]2[C@@H]([C@H]2C(O)=O)[C@]1(N)C(O)=O)SC1=CC=C(F)C(Cl)=C1 GTHAIOYBHQWJIR-XJDZXMJWSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 208000032140 Sleepiness Diseases 0.000 claims 1
- 206010041349 Somnolence Diseases 0.000 claims 1
- GWNLIFCQSNMZAQ-SVCRZZQPSA-N bis(propan-2-yloxycarbonyloxymethyl) (1s,2r,3s,4s,5r,6r)-2-amino-3-[(3,4-difluorophenyl)sulfanylmethyl]-4-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylate Chemical compound C([C@H]1[C@](N)([C@H]2[C@@H]([C@@H]1O)[C@@H]2C(=O)OCOC(=O)OC(C)C)C(=O)OCOC(=O)OC(C)C)SC1=CC=C(F)C(F)=C1 GWNLIFCQSNMZAQ-SVCRZZQPSA-N 0.000 claims 1
- FIDMVEHTSPSEOQ-SVCRZZQPSA-N bis(propan-2-yloxycarbonyloxymethyl) (1s,2r,3s,4s,5r,6r)-2-amino-3-[(3-chloro-4-fluorophenyl)sulfanylmethyl]-4-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylate Chemical compound C([C@H]1[C@](N)([C@H]2[C@@H]([C@@H]1O)[C@@H]2C(=O)OCOC(=O)OC(C)C)C(=O)OCOC(=O)OC(C)C)SC1=CC=C(F)C(Cl)=C1 FIDMVEHTSPSEOQ-SVCRZZQPSA-N 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 230000037321 sleepiness Effects 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
- C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
-
- 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
- A61K31/095—Sulfur, selenium, or tellurium compounds, e.g. thiols
- A61K31/10—Sulfides; Sulfoxides; Sulfones
-
- 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
- A61P25/24—Antidepressants
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/14—All rings being cycloaliphatic
- C07C2602/18—All rings being cycloaliphatic the ring system containing six carbon atoms
Claims (16)
1. Spoj formule
[image]
,
naznačen time što
svaki od R1 i R2 je neovisno vodik, C1-C3 alkoksikarboniloksimetil, C1-C5 alkilkarboniloksimetil ili C3-6 cikloalkilkarboniloksimetil;
R3 je svaki put neovisno metil, fluor ili klor;
R4 je hidroksil, amino, metilkarbonilamino ili 1,2,4-triazoliltio; i
n je 1 ili 2;
ili njegova farmaceutski prihvatljiva sol.
2. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je svaki od R1 i R2 vodik, ili njegova farmaceutski prihvatljiva sol.
3. Spoj u skladu s patentnim zahtjevom 1, naznačen time što su R1 i R2 isti i nisu vodici, ili njegova farmaceutski prihvatljiva sol.
4. Spoj u skladu s patentnim zahtjevom 3, naznačen time što je svaki od R1 i R2 izopropiloksikarboniloksimetil.
5. Spoj u skladu s bilo kojim do patentnih zahtjeva 1 do 4, naznačen time što je n 2, a skupine R3 su na položajima 3 i 4 u fenilu.
6. Spoj u skladu s bilo kojim do patentnih zahtjeva 1 do 5, naznačen time što je R3 svaki put neovisno klor ili fluor.
7. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je (1S,2R,3S,4S,5R,6R)-2-amino-3-{[(3,4-difluorfenil)sulfanil]metil}-4-hidroksibiciklo[3.1.0]heksan-2,6-dikarboksila kiselina, ili njezina farmaceutski prihvatljiva sol.
8. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je bis({[(1-metiletoksi)karbonil]oksi}metil)-(1S,2R,3S,4S,5R,6R)-2-amino-3-{[(3,4-difluorfenil)sulfanil]metil}-4-hidroksibiciklo[3.1.0]heksan-2,6-dikarboksilat, ili njegova farmaceutski prihvatljiva sol.
9. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je (1S,2R,3S,4S,5R,6R)-2-amino-3-{[(3-klor-4-fluorfenil)sulfanil]metil}-4-hidroksibiciklo[3.1.0]heksan-2,6-dikarboksila kiselina, ili njezina farmaceutski prihvatljiva sol.
10. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je bis({[(1-metiletoksi)karbonil]oksi}metil)-(1S,2R,3S,4S,5R,6R)-2-amino-3-{[(3-klor-4-fluorfenil)sulfanil]metil}-4-hidroksibiciklo[3.1.0]heksan-2,6-dikarboksilat, ili njegova farmaceutski prihvatljiva sol.
11. Farmaceutski pripravak, naznačen time što sadrži spoj u skladu s bilo kojim do patentnih zahtjeva 1 do 10, ili njegova farmaceutski prihvatljiva sol, u kombinaciji s najmanje jednom farmaceutski prihvatljivom podlogom, pomoćnom tvari ili razrjeđivačem.
12. Spoj u skladu s bilo kojim do patentnih zahtjeva 1 do 10, ili njegova farmaceutski prihvatljiva sol, naznačen time što je namijenjen upotrebi u terapiji.
13. Spoj u skladu s bilo kojim do patentnih zahtjeva 1 do 10, ili njegova farmaceutski prihvatljiva sol, naznačen time što je namijenjen upotrebi u liječenju depresivnih poremećaja.
14. Spoj u skladu s bilo kojim do patentnih zahtjeva 1 do 10, ili njegova farmaceutski prihvatljiva sol, naznačen time što je namijenjen upotrebi u liječenju poremećaja prekomjerne pospanosti.
15. Spoj u skladu s bilo kojim do patentnih zahtjeva 1 do 10, ili njegova farmaceutski prihvatljiva sol, naznačen time što je namijenjen upotrebi u istodobnoj, odvojenoj ili uzastopnoj kombinaciji s inhibitorom povratnog unosa serotonina u liječenju depresivnih poremećaja.
16. Farmaceutski pripravak u skladu s patentnim zahtjevom 11, naznačen time što pripravak dodatno sadrži inhibitor povratnog unosa serotonina.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41512110P | 2010-11-18 | 2010-11-18 | |
| EP11791692.4A EP2640697B1 (en) | 2010-11-18 | 2011-11-15 | 4-substituted-3-phenylsulfanylmethyl-bicyclo[3.1.0]hexane compounds as mglur 2/3 antagonists |
| PCT/US2011/060730 WO2012068067A1 (en) | 2010-11-18 | 2011-11-15 | 4-substituted-3-phenylsulfanylmethyl-bicyclo[3.1.0]hexane compounds as mglur 2/3 antagonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20171649T1 true HRP20171649T1 (hr) | 2017-12-15 |
Family
ID=45099188
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20171649TT HRP20171649T1 (hr) | 2010-11-18 | 2017-10-27 | 4-supstituirani spojevi 3-fenilsulfanilmetilbiciklo[3.1.0]heksana kao antagonisti mglur 2/3 |
Country Status (36)
| Country | Link |
|---|---|
| US (1) | US8629169B2 (hr) |
| EP (1) | EP2640697B1 (hr) |
| JP (1) | JP5877847B2 (hr) |
| KR (2) | KR20150140876A (hr) |
| CN (1) | CN103228625B (hr) |
| AR (1) | AR083845A1 (hr) |
| AU (1) | AU2011329076B2 (hr) |
| BR (1) | BR112013012118A2 (hr) |
| CA (1) | CA2818116C (hr) |
| CL (1) | CL2013001345A1 (hr) |
| CO (1) | CO6761385A2 (hr) |
| CR (1) | CR20130178A (hr) |
| DK (1) | DK2640697T3 (hr) |
| DO (1) | DOP2013000099A (hr) |
| EA (1) | EA021724B1 (hr) |
| EC (1) | ECSP13012629A (hr) |
| ES (1) | ES2650139T3 (hr) |
| GT (1) | GT201300126A (hr) |
| HR (1) | HRP20171649T1 (hr) |
| HU (1) | HUE037457T2 (hr) |
| IL (1) | IL225843A (hr) |
| LT (1) | LT2640697T (hr) |
| MA (1) | MA34663B1 (hr) |
| MX (1) | MX339973B (hr) |
| NO (1) | NO2640697T3 (hr) |
| NZ (1) | NZ609816A (hr) |
| PE (1) | PE20140997A1 (hr) |
| PL (1) | PL2640697T3 (hr) |
| PT (1) | PT2640697T (hr) |
| RS (1) | RS56535B1 (hr) |
| SG (1) | SG189959A1 (hr) |
| SI (1) | SI2640697T1 (hr) |
| TW (1) | TWI520935B (hr) |
| UA (1) | UA110039C2 (hr) |
| WO (1) | WO2012068067A1 (hr) |
| ZA (1) | ZA201302918B (hr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JO2978B1 (en) * | 2009-12-21 | 2016-03-15 | ايلي ليلي اند كومباني | MGLU2 aids |
| EP3000814A1 (en) | 2014-09-26 | 2016-03-30 | Domain Therapeutics | Substituted pyrazoloquinazolinones and pyrroloquinazolinones as allosteric modulators of group II metabotropic glutamate receptors |
| DK3445743T3 (da) | 2016-04-18 | 2021-10-18 | Taisho Pharmaceutical Co Ltd | Prodrug af aminosyrederivat |
| JP2020506895A (ja) | 2017-01-17 | 2020-03-05 | ボード オブ レジェンツ, ザ ユニバーシティ オブ テキサス システムBoard Of Regents, The University Of Texas System | インドールアミン２，３−ジオキシゲナーゼおよび／またはトリプトファンジオキシゲナーゼの阻害剤として有用な化合物 |
| US11046649B2 (en) | 2018-07-17 | 2021-06-29 | Board Of Regents, The University Of Texas System | Compounds useful as inhibitors of indoleamine 2,3-dioxygenase and/or tryptophan dioxygenase |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0669928B2 (ja) | 1987-10-06 | 1994-09-07 | 宇部興産株式会社 | 光重合性歯科材料 |
| JP2589812B2 (ja) | 1989-07-05 | 1997-03-12 | 松下電器産業株式会社 | スチームアイロン |
| EA000894B1 (ru) * | 1995-11-16 | 2000-06-26 | Эли Лилли Энд Компани | Замещенные бициклогексанкарбоновые кислоты и их производные в качестве антагонистов рецептора возбуждающих аминокислот, способ их получения и применение |
| ZA969485B (en) | 1995-11-16 | 1998-05-12 | Lilly Co Eli | Excitatory amino acid receptor antagonists. |
| ZA983930B (en) * | 1997-05-14 | 1999-11-08 | Lilly Co Eli | Excitatory amino acid receptor modulators. |
| EP1064256B1 (en) * | 1998-03-17 | 2004-08-04 | Pfizer Products Inc. | Bicyclo [2.2.1] heptanes and related compounds |
| GB9815542D0 (en) | 1998-07-17 | 1998-09-16 | Lilly Co Eli | Bicyclohexane derivatives |
| CH694053A5 (de) | 1998-09-03 | 2004-06-30 | Hoffmann La Roche | Verfahren zur Herstellung von 2-Amino-bicyclo[3.1.0]hexan-2,6-dicarbonsäure-Derivaten. |
| WO2002068380A1 (en) * | 2001-02-22 | 2002-09-06 | Eli Lilly And Company | Synthetic excitatory amino acids |
| AU2002359923B2 (en) | 2001-12-27 | 2007-12-20 | Taisho Pharmaceutical Co., Ltd. | 6-fluorobicyclo[3.1.0]hexane derivatives |
| PT1517915E (pt) * | 2002-06-11 | 2009-04-09 | Lilly Co Eli | Pró-drogas de amino ácidos de excitação |
| NZ580554A (en) * | 2003-06-26 | 2011-01-28 | Taisho Pharmaceutical Co Ltd | 2-Aminobicyclo[3.1.0]hexane-2,6-dicarboxylic ester derivative |
| JP2007063129A (ja) | 2003-06-26 | 2007-03-15 | Taisho Pharmaceut Co Ltd | ２−アミノ−３−アルコキシビシクロ［３．１．０］ヘキサン誘導体 |
| WO2005000790A1 (ja) * | 2003-06-26 | 2005-01-06 | Taisho Pharmaceutical Co., Ltd. | ２－アミノビシクロ[３．１．０]ヘキサン－２，６－ジカルボン酸誘導体 |
| JO2978B1 (en) * | 2009-12-21 | 2016-03-15 | ايلي ليلي اند كومباني | MGLU2 aids |
-
2011
- 2011-11-11 AR ARP110104219A patent/AR083845A1/es unknown
- 2011-11-11 TW TW100141326A patent/TWI520935B/zh not_active IP Right Cessation
- 2011-11-15 EA EA201390498A patent/EA021724B1/ru not_active IP Right Cessation
- 2011-11-15 RS RS20171082A patent/RS56535B1/sr unknown
- 2011-11-15 HU HUE11791692A patent/HUE037457T2/hu unknown
- 2011-11-15 BR BR112013012118A patent/BR112013012118A2/pt not_active IP Right Cessation
- 2011-11-15 WO PCT/US2011/060730 patent/WO2012068067A1/en active Application Filing
- 2011-11-15 LT LTEP11791692.4T patent/LT2640697T/lt unknown
- 2011-11-15 NO NO11791692A patent/NO2640697T3/no unknown
- 2011-11-15 DK DK11791692.4T patent/DK2640697T3/en active
- 2011-11-15 MX MX2013005622A patent/MX339973B/es active IP Right Grant
- 2011-11-15 SG SG2013030507A patent/SG189959A1/en unknown
- 2011-11-15 KR KR1020157034547A patent/KR20150140876A/ko not_active Application Discontinuation
- 2011-11-15 CN CN201180055263.7A patent/CN103228625B/zh active Active
- 2011-11-15 JP JP2013539938A patent/JP5877847B2/ja active Active
- 2011-11-15 ES ES11791692.4T patent/ES2650139T3/es active Active
- 2011-11-15 AU AU2011329076A patent/AU2011329076B2/en not_active Ceased
- 2011-11-15 KR KR1020137012697A patent/KR20130101094A/ko active IP Right Grant
- 2011-11-15 PT PT117916924T patent/PT2640697T/pt unknown
- 2011-11-15 NZ NZ609816A patent/NZ609816A/en not_active IP Right Cessation
- 2011-11-15 US US13/296,384 patent/US8629169B2/en active Active
- 2011-11-15 PL PL11791692T patent/PL2640697T3/pl unknown
- 2011-11-15 PE PE2013001215A patent/PE20140997A1/es not_active Application Discontinuation
- 2011-11-15 EP EP11791692.4A patent/EP2640697B1/en active Active
- 2011-11-15 UA UAA201305835A patent/UA110039C2/ru unknown
- 2011-11-15 SI SI201131304T patent/SI2640697T1/sl unknown
- 2011-11-15 CA CA2818116A patent/CA2818116C/en active Active
-
2013
- 2013-04-18 IL IL225843A patent/IL225843A/en not_active IP Right Cessation
- 2013-04-22 ZA ZA2013/02918A patent/ZA201302918B/en unknown
- 2013-04-24 CR CR20130178A patent/CR20130178A/es unknown
- 2013-05-08 DO DO2013000099A patent/DOP2013000099A/es unknown
- 2013-05-13 MA MA35898A patent/MA34663B1/fr unknown
- 2013-05-15 GT GT201300126A patent/GT201300126A/es unknown
- 2013-05-15 CL CL2013001345A patent/CL2013001345A1/es unknown
- 2013-05-17 EC ECSP13012629 patent/ECSP13012629A/es unknown
- 2013-05-30 CO CO13133036A patent/CO6761385A2/es unknown
-
2017
- 2017-10-27 HR HRP20171649TT patent/HRP20171649T1/hr unknown
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