HRP20210040T1 - (2r,4r)-5-(5′-klor-2’-fluorbifenil-4-il)-2-hidroksi-4-[(5-metiloksazol-2-karbonil)amino]pentanska kiselina - Google Patents
(2r,4r)-5-(5′-klor-2’-fluorbifenil-4-il)-2-hidroksi-4-[(5-metiloksazol-2-karbonil)amino]pentanska kiselina Download PDFInfo
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- HRP20210040T1 HRP20210040T1 HRP20210040TT HRP20210040T HRP20210040T1 HR P20210040 T1 HRP20210040 T1 HR P20210040T1 HR P20210040T T HRP20210040T T HR P20210040TT HR P20210040 T HRP20210040 T HR P20210040T HR P20210040 T1 HRP20210040 T1 HR P20210040T1
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- Prior art keywords
- crystalline form
- compound
- compound according
- methyloxazole
- fluorobiphenyl
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- RRCIEZCEOIRHEB-VQIMIIECSA-N (2R,4R)-5-[4-(5-chloro-2-fluorophenyl)phenyl]-2-hydroxy-4-[(5-methyl-1,3-oxazole-2-carbonyl)amino]pentanoic acid Chemical compound ClC=1C=CC(=C(C=1)C1=CC=C(C=C1)C[C@H](C[C@H](C(=O)O)O)NC(=O)C=1OC(=CN=1)C)F RRCIEZCEOIRHEB-VQIMIIECSA-N 0.000 title claims 3
- 150000001875 compounds Chemical class 0.000 claims 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims 5
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 230000005855 radiation Effects 0.000 claims 3
- ODPPPGVWSBDXFN-UHFFFAOYSA-N 5-methyl-1,3-oxazole-2-carboxylic acid Chemical compound CC1=CN=C(C(O)=O)O1 ODPPPGVWSBDXFN-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 2
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 claims 2
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 208000017169 kidney disease Diseases 0.000 claims 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical group [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims 2
- 238000000634 powder X-ray diffraction Methods 0.000 claims 2
- 239000007787 solid Substances 0.000 claims 2
- 238000003756 stirring Methods 0.000 claims 2
- JRHWHSJDIILJAT-UHFFFAOYSA-N 2-hydroxypentanoic acid Chemical compound CCCC(O)C(O)=O JRHWHSJDIILJAT-UHFFFAOYSA-N 0.000 claims 1
- 239000005541 ACE inhibitor Substances 0.000 claims 1
- 101710129690 Angiotensin-converting enzyme inhibitor Proteins 0.000 claims 1
- 101710086378 Bradykinin-potentiating and C-type natriuretic peptides Proteins 0.000 claims 1
- 239000007821 HATU Substances 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- -1 N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate Chemical compound 0.000 claims 1
- 239000002333 angiotensin II receptor antagonist Substances 0.000 claims 1
- 239000000400 angiotensin II type 1 receptor blocker Substances 0.000 claims 1
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims 1
- 239000008366 buffered solution Substances 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 208000020832 chronic kidney disease Diseases 0.000 claims 1
- 230000021615 conjugation Effects 0.000 claims 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 claims 1
- 239000002934 diuretic Substances 0.000 claims 1
- 230000001882 diuretic effect Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- WDBBEKDVFVFYRC-CRAIPNDOSA-N ethyl (2r,4r)-4-amino-5-[4-(5-chloro-2-fluorophenyl)phenyl]-2-hydroxypentanoate Chemical compound C1=CC(C[C@@H](N)C[C@@H](O)C(=O)OCC)=CC=C1C1=CC(Cl)=CC=C1F WDBBEKDVFVFYRC-CRAIPNDOSA-N 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 230000024924 glomerular filtration Effects 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 230000001771 impaired effect Effects 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 239000006207 intravenous dosage form Substances 0.000 claims 1
- 201000006370 kidney failure Diseases 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 235000019359 magnesium stearate Nutrition 0.000 claims 1
- 239000006186 oral dosage form Substances 0.000 claims 1
- 208000002815 pulmonary hypertension Diseases 0.000 claims 1
- 239000002461 renin inhibitor Substances 0.000 claims 1
- 229940086526 renin-inhibitors Drugs 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 239000003826 tablet Substances 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
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
- A61K31/41—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
- A61K31/42—Oxazoles
- A61K31/421—1,3-Oxazoles, e.g. pemoline, trimethadione
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4816—Wall or shell material
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4816—Wall or shell material
- A61K9/4825—Proteins, e.g. gelatin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- 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
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- 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
-
- 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
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- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
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- 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
- A61P9/12—Antihypertensives
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- C—CHEMISTRY; METALLURGY
- C30—CRYSTAL GROWTH
- C30B—SINGLE-CRYSTAL GROWTH; UNIDIRECTIONAL SOLIDIFICATION OF EUTECTIC MATERIAL OR UNIDIRECTIONAL DEMIXING OF EUTECTOID MATERIAL; REFINING BY ZONE-MELTING OF MATERIAL; PRODUCTION OF A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; SINGLE CRYSTALS OR HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; AFTER-TREATMENT OF SINGLE CRYSTALS OR A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; APPARATUS THEREFOR
- C30B29/00—Single crystals or homogeneous polycrystalline material with defined structure characterised by the material or by their shape
- C30B29/54—Organic compounds
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- C—CHEMISTRY; METALLURGY
- C30—CRYSTAL GROWTH
- C30B—SINGLE-CRYSTAL GROWTH; UNIDIRECTIONAL SOLIDIFICATION OF EUTECTIC MATERIAL OR UNIDIRECTIONAL DEMIXING OF EUTECTOID MATERIAL; REFINING BY ZONE-MELTING OF MATERIAL; PRODUCTION OF A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; SINGLE CRYSTALS OR HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; AFTER-TREATMENT OF SINGLE CRYSTALS OR A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; APPARATUS THEREFOR
- C30B7/00—Single-crystal growth from solutions using solvents which are liquid at normal temperature, e.g. aqueous solutions
- C30B7/14—Single-crystal growth from solutions using solvents which are liquid at normal temperature, e.g. aqueous solutions the crystallising materials being formed by chemical reactions in the solution
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- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
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- C07B2200/13—Crystalline forms, e.g. polymorphs
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- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Metallurgy (AREA)
- Crystallography & Structural Chemistry (AREA)
- Materials Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Medicinal Preparation (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (17)
1. Spoj, naznačen time što je (2R,4R)-5-(5′-klor-2′-fluorbifenil-4-il)-2-hidroksi-4-[(5-metiloksazol-2-karbonil)amino]pentanska kiselina sa strukturom:
[image]
,
ili farmaceutski njezina prihvatljiva sol.
2. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je kristalni oblik (2R,4R)-5-(5′-klor-2′-fluorbifenil-4-il)-2-hidroksi-4-[(5-metiloksazol-2-karbonil)amino]pentanske kiseline.
3. Kristalni oblik u skladu s patentnim zahtjevom 2, gdje je kristalni oblik naznačen time što ima uzorak difrakcije rendgenskih zraka na prahu koji sadrži maksimume difrakcije kod vrijednosti 2θ od 8,48 ± 0,20, 14,19 ± 0,20, 17,03 ± 0,20, 21,15 ± 0,20, te 25,41 ± 0,20, gdje su vrijednosti 2θ dobivene uz pomoć zračenja Cu-Kα.
4. Kristalni oblik u skladu s patentnim zahtjevom 3, gdje je kristalni oblik naznačen time što ima uzorak difrakcije rendgenskih zraka na prahu koji sadrži maksimume difrakcije kod vrijednosti 2θ od 7,51 ± 0,20, 8,48 ± 0,20, 14,19 ± 0,20, 17,03 ± 0,20, 17,62 ± 0,20, 17,87 ± 0,20, 20,59 ± 0,20, 21,15 ± 0,20, 21,88 ± 0,20, 24,45 ± 0,20, 24,78 ± 0,20, 25,41 ± 0,20, 25,67 ± 0,20, 27,67 ± 0,20, te 28,22 ± 0,20, gdje su vrijednosti 2θ dobivene uz pomoć zračenja Cu-Kα.
5. Kristalni oblik u skladu s patentnim zahtjevom 4, gdje je kristalni oblik naznačen time što dodatno ima jedan ili više dodatnih maksimuma difrakcije kod vrijednosti 2θ, koje se bira između 16,09 ± 0,20, 18,70 ± 0,20, 19,21 ± 0,20, 19,40 ± 0,20, 21,64 ± 0,20, 22,25 ± 0,20, 26,43 ± 0,20, 28,55 ± 0,20, 30,73 ± 0,20, 31,10 ± 0,20, 32,64 ± 0,20, 33,14 ± 0,20, te 34,46 ± 0,20, gdje su vrijednosti 2θ dobivene uz pomoć zračenja Cu-Kα.
6. Kristalni oblik u skladu s patentnim zahtjevom 2, gdje je kristalni oblik naznačen time što ima krivulju diferencijalne skenirajuće kalorimetrija zabilježenu pri brzini grijanja od 10 °C u minuti, koja prikazuje maksimum u endotermnom toplinskom toku na temperaturi između 165 °C i 169 °C.
7. Farmaceutski pripravak, naznačen time što sadrži spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 6, kao i jedan ili više farmaceutski prihvatljivih nosača, izborno zajedno s drugim terapijskim sredstvom.
8. Farmaceutski pripravak u skladu s patentnim zahtjevom 7, naznačen time što je farmaceutski prihvatljivi nosač magnezijev stearat.
9. Farmaceutski pripravak u skladu s patentnim zahtjevom 7, naznačen time što sadrži antagonist receptora AT1, inhibitor angiotensin-konvertirajućeg enzima, inhibitor fosfodiesteraze (PDE), inhibitor renin, diuretik, ili njihove kombinacije.
10. Farmaceutski pripravak u skladu s patentnim zahtjevom 7, naznačen time što je oralni oblik doziranja koji sadrži spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 6 u kapsuli, tableti, tekućini ili suspenziji.
11. Farmaceutski pripravak u skladu s patentnim zahtjevom 7, naznačen time što je intravenski oblik doziranja koji sadrži spoj u skladu s patentnim zahtjevom 1 u puferiranoj otopini.
12. Postupak priprave spoja u skladu s patentnim zahtjevom 1, naznačen time što se postupak sastoji u konjugiranju etilnog estera (2R,4R)-4-amino-5-(5’-klor-2′-fluorbifenil-4-il)-2-hidroksipentanske kiseline s 5-metiloksazol-2-karboksilnom kiselinom kako bi se dobilo spoj u skladu s patentnim zahtjevom 1.
13. Postupak u skladu s patentnim zahtjevom 12, naznačen time što se sastoji u:
(a) kombiniranju 5-metiloksazol-2-karboksilne kiseline s N,N,N′,N′-tetrametil-O-(7-azabenzotriazol-1-il)uronijevim heksafluorofosfatom (HATU) u N,N-dimetilformamidu (DMF) uz miješanje na sobnoj temperaturi;
(b) dodavanju etilnog estera (2R,4R)-4-amino-5-(5′-klor-2′-fluorbifenil-4-il)-2-hidroksipentanske kiseline i N,N-diizopropiletilamina uz miješanje na sobnoj temperaturi;
(c) izoliranju, te zatim otapanju nastalih krutina u suhom etanolu i suhom tetrahidrofuranu;
(d) dodavanju otopine litijevog hidroksida u vodi; i
(e) izoliranju nastalih krutina kako bi se dobilo spoj u skladu s patentnim zahtjevom 1.
14. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 6, naznačen time što je namijenjen upotrebi u terapiji.
15. Spoj namijenjen upotrebi u skladu s patentnim zahtjevom 14, naznačen time što je namijenjen upotrebi u liječenju hipertenzije, plućne hipertenzija, zatajenja srca ili bubrežne bolesti.
16. Spoj namijenjen upotrebi u skladu s patentnim zahtjevom 14, naznačen time što je namijenjen upotrebi u subjekt s poremećajem bubrega.
17. Spoj namijenjen upotrebi u skladu s patentnim zahtjevom 16, naznačen time što je namijenjen upotrebi u liječenju subjekta s poremećajem bubrega koji ima kroničnu bolest bubrega s procijenjenom stopa filtriranja u glomerulima (eGFR) između 60 ml/min/1,73 m2 i 15 ml/min/1,73 m2.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562118067P | 2015-02-19 | 2015-02-19 | |
| PCT/US2016/017699 WO2016133803A1 (en) | 2015-02-19 | 2016-02-12 | (2r,4r)-5-(5'-chloro-2'-fluorobiphenyl-4-yl)-2-hydroxy-4-[(5-methyloxazole-2-carbonyl)amino]pentanoic acid |
| EP16708268.4A EP3259255B1 (en) | 2015-02-19 | 2016-02-12 | (2r,4r)-5-(5'-chloro-2'-fluorobiphenyl-4-yl)-2-hydroxy-4-[(5-methyloxazole-2-carbonyl)amino]pentanoic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20210040T1 true HRP20210040T1 (hr) | 2021-04-02 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20210040TT HRP20210040T1 (hr) | 2015-02-19 | 2021-01-11 | (2r,4r)-5-(5′-klor-2’-fluorbifenil-4-il)-2-hidroksi-4-[(5-metiloksazol-2-karbonil)amino]pentanska kiselina |
Country Status (29)
| Country | Link |
|---|---|
| US (6) | US9533962B2 (hr) |
| EP (1) | EP3259255B1 (hr) |
| JP (1) | JP6714009B2 (hr) |
| KR (1) | KR102573351B1 (hr) |
| CN (1) | CN107250119B (hr) |
| AU (1) | AU2016220348B2 (hr) |
| BR (1) | BR112017017783A2 (hr) |
| CA (1) | CA2975269C (hr) |
| CO (1) | CO2017008426A2 (hr) |
| CY (1) | CY1123728T1 (hr) |
| DK (1) | DK3259255T3 (hr) |
| ES (1) | ES2857101T3 (hr) |
| HK (1) | HK1245772A1 (hr) |
| HR (1) | HRP20210040T1 (hr) |
| HU (1) | HUE052732T2 (hr) |
| IL (1) | IL253759B (hr) |
| LT (1) | LT3259255T (hr) |
| MX (1) | MX370065B (hr) |
| MY (1) | MY191183A (hr) |
| PH (1) | PH12017501444A1 (hr) |
| PL (1) | PL3259255T3 (hr) |
| PT (1) | PT3259255T (hr) |
| RS (1) | RS61325B1 (hr) |
| RU (1) | RU2715241C2 (hr) |
| SG (1) | SG11201706662YA (hr) |
| SI (1) | SI3259255T1 (hr) |
| TW (1) | TWI707846B (hr) |
| WO (1) | WO2016133803A1 (hr) |
| ZA (1) | ZA201705487B (hr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2013271537B2 (en) * | 2012-06-08 | 2017-05-11 | Theravance Biopharma R&D Ip, Llc | Neprilysin inhibitors |
| JP6714009B2 (ja) | 2015-02-19 | 2020-06-24 | セラヴァンス バイオファーマ アール＆ディー アイピー， エルエルシー | （２ｒ，４ｒ）−５−（５’−クロロ−２’−フルオロビフェニル−４−イル）−２−ヒドロキシ−４−［（５−メチルオキサゾール−２−カルボニル）アミノ］ペンタン酸 |
| KR102238177B1 (ko) | 2017-09-15 | 2021-04-07 | 주식회사 엘지화학 | 전지셀 및 전극 리드 제조방법 |
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