HRP20160389T1 - Derivati orvinola i tevinola korisni u liječenju bolesti ovisnosti o drogama i alkoholu - Google Patents
Derivati orvinola i tevinola korisni u liječenju bolesti ovisnosti o drogama i alkoholu Download PDFInfo
- Publication number
- HRP20160389T1 HRP20160389T1 HRP20160389TT HRP20160389T HRP20160389T1 HR P20160389 T1 HRP20160389 T1 HR P20160389T1 HR P20160389T T HRP20160389T T HR P20160389TT HR P20160389 T HRP20160389 T HR P20160389T HR P20160389 T1 HRP20160389 T1 HR P20160389T1
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- HR
- Croatia
- Prior art keywords
- compound
- pharmaceutically acceptable
- solvate
- compound according
- acceptable salt
- Prior art date
Links
- 208000011117 substance-related disease Diseases 0.000 title claims 3
- 208000007848 Alcoholism Diseases 0.000 title 1
- 206010013654 Drug abuse Diseases 0.000 title 1
- 206010001584 alcohol abuse Diseases 0.000 title 1
- 208000025746 alcohol use disease Diseases 0.000 title 1
- 239000003814 drug Substances 0.000 title 1
- 229940079593 drug Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 25
- 150000003839 salts Chemical class 0.000 claims 11
- 239000012453 solvate Substances 0.000 claims 11
- 230000015572 biosynthetic process Effects 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 238000003786 synthesis reaction Methods 0.000 claims 3
- 239000002841 Lewis acid Substances 0.000 claims 2
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 150000007517 lewis acids Chemical class 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- -1 17 -cyclopropylmethyl-6,14-etheno-morphinan-7-yl Chemical group 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000020401 Depressive disease Diseases 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D489/00—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
- C07D489/09—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: containing 4aH-8, 9 c-Iminoethano- phenanthro [4, 5-b, c, d] furan ring systems condensed with carbocyclic rings or ring systems
- C07D489/10—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: containing 4aH-8, 9 c-Iminoethano- phenanthro [4, 5-b, c, d] furan ring systems condensed with carbocyclic rings or ring systems with a bridge between positions 6 and 14
- C07D489/12—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: containing 4aH-8, 9 c-Iminoethano- phenanthro [4, 5-b, c, d] furan ring systems condensed with carbocyclic rings or ring systems with a bridge between positions 6 and 14 the bridge containing only two carbon atoms
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4748—Quinolines; Isoquinolines forming part of bridged ring systems
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/485—Morphinan derivatives, e.g. morphine, codeine
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D489/00—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
- C07D489/09—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: containing 4aH-8, 9 c-Iminoethano- phenanthro [4, 5-b, c, d] furan ring systems condensed with carbocyclic rings or ring systems
- C07D489/10—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: containing 4aH-8, 9 c-Iminoethano- phenanthro [4, 5-b, c, d] furan ring systems condensed with carbocyclic rings or ring systems with a bridge between positions 6 and 14
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/08—Bridged systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Addiction (AREA)
- Epidemiology (AREA)
- Psychiatry (AREA)
- Emergency Medicine (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (20)
1. Spoj čija je formula 2, ili farmaceutski prihvatljiva sol ili solvat tog spoja
[image]
u kome
R je H
R1 je ciklopropilmetil
R2 je H
R4 i R5 su metil
R3 je aril ili heteroaril od kojih svaki može biti supstituiran ili nesupstituiran, i
X je zasićeni most (-CH2CH2-) ili nezasićeni most (-CH=CH-).
2. Spoj prema patentnom zahtjevu 1, u kome R3 je fenil, po izboru supstituiran sa halogen, metil, hidroksil ili metoksi.
3. Spoj prema patentnom zahtjevu 1, u kome R3 je fenil.
4. Spoj prema patentnom zahtjevu 1, u kome R3 je heteroaril.
5. Spoj prema bilo kojem prethodnom patentnom zahtjevu u kome X je CH2CH2
6. Spoj prema bilo kojem prethodnom patentnom zahtjevu u kome X je CH=CH
7. Metoda za sintezu spoja čija je formula 2
[image]
u kome
R je H
R1 je ciklopropilmetil
R2 je H
R4 i R5 su metil
R3 je aril ili heteroaril od kojih svaki može biti supstituiran ili nesupstituiran i
X je zasićeni most (-CH2CH2-) ili nezasićeni most (-CH=CH-), metoda sadrži korak kombiniranja N-acilnortebaina sa metakroleinom u prisustvu Lewis kiseline kao katalizatora.
8. Metoda za sintezu spoja čija je struktura 3 kao posrednik u sintezi spoja patentnog zahtjeva 1, kombiniranjem N-ciklopropilkarbonilnortebaina sa metakroleinom u prisustvu Lewis kiseline kao katalizatora.
[image]
9. Kompozicija koja sadrži Spoj prema bilo kojem od patentnih zahtjeva 1 do 6, ili farmaceutski prihvatljivu sol ili solvat tog spoja, i farmaceutski prihvatljiv ekscipijens ili nosač.
10. Spoj prema bilo kojem od patentnih zahtjeva 1 to 6 ili farmaceutski prihvatljiva sol ili solvat tog spoja za primjenu u liječenju.
11. Spoj prema patentnom zahtjevu 10 za primjenu u liječenju bolesti ovisnosti o supstanci, poželjno za primjenu u prevenciji povratka bolesti ovisnosti o supstanci.
12. Spoj prema patentnom zahtjevu 10 za primjenu u liječenju depresije, anksioznosti ili kompulzivnih poremećaja.
13. Spoj koje je (1'S, 5α, 6R, 7R, 14α)-1'-fenil-1'-(4,5-epoksi-7,8-dihidro-3-hidroksi-6-metoksi-17-ciklopropilmetil-6,14-etano-morfinan-7-il)-etan-1'-ol ili farmaceutski prihvatljiva sol ili solvat tog spoja.
14. Spoj koji je (1'S, 5α, 6R, 7R, 14α)-1'-fenil-1'-(4,5-epoksi-7,8-dihidro-3-hidroksi-6-metoksi-17-ciklopropilmetil-6,14-etanomorfinan-7-il)-metan-1'-ol ili farmaceutski prihvatljiva sol ili solvat tog spoja.
15. Spoj prema patentnom zahtjevu 1 koji je (1'R, 5α, 6R, 7R, 14α)-1'-fenil-1'-(4,5-epoksi-7,8-dihidro-3-hidroksi-6-metoksi-7β-metil 17-ciklopropilmetil-6,14-etenomorfinan-7-il)-metan-1'-ol ili farmaceutski prihvatljiva sol ili solvat tog spoja.
16. Spoj koji je (1'S, 5α, 6R, 7R, 14α)-1'-fenil-1'-(4,5-epoksi-7,8-dihidro-3-hidroksi-6-metoksi-7β-metil 17-ciklopropilmetil-6,14-eteno-morfinan-7-il)-metan-1'-ol ili farmaceutski prihvatljiva sol ili solvat tog spoja.
17. Spoj koji je (1'S, 5α, 6R, 7R, 14α)-1'-fenil-1'-(4,5-epoksi-7,8-dihidro-3-hidroksi-6-metoksi-17-ciklopropilmetil-6,14-etenomorfinan-7-il)-metan-1'-ol ili farmaceutski prihvatljiva sol ili solvat tog spoja.
18. Spoj prema patentnom zahtjevu 1 koji je (1'R, 5α, 6R, 7R, 14α)-1'-(3-metilfenil)-1'-(4,5-epoksi-7,8-dihidro-3-hidroksi-6-metoksi-7β-metil17-ciklopropilmetil-6,14-eteno-morfinan-7-il)-metan-1'-ol ili farmaceutski prihvatljiva sol ili solvat tog spoja.
19. Spoj prema patentnom zahtjevu 1 koji je (1'R, 5α, 6R, 7R, 14α)-1'-fenil-1'-(4,5-epoksi-7,8-dihidro-3-hidroksi-6-metoksi-7β-metil 17-ciklopropilmetil-6,14-etanomorfinan-7-il)-metan-1'-ol; ili farmaceutski prihvatljiva sol ili solvat tog spoja.
20. Spoj prema patentnom zahtjevu 1 koji je (1'R, 5α, 6R, 7R, 14α)-1'-(4-fluorofenil)-1'-(4,5-epoksi-7,8-dihidro-3-hidroksi-6-metoksi-7β-metil 17-ciklopropilmetil-6,14-eteno-morfinan-7-il)-metan-1'-ol ili farmaceutski prihvatljiva sol ili solvat tog spoja.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1111775.1A GB201111775D0 (en) | 2011-07-08 | 2011-07-08 | Compounds and uses thereof |
| PCT/GB2012/051575 WO2013007986A1 (en) | 2011-07-08 | 2012-07-05 | Orvinol and thevinol derivatives useful in the treatment of drug and alcohol abuse |
| EP12735607.9A EP2729469B1 (en) | 2011-07-08 | 2012-07-05 | Orvinol and thevinol derivatives useful in the treatment of drug and alcohol abuse |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20160389T1 true HRP20160389T1 (hr) | 2016-07-01 |
Family
ID=44544490
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20160389TT HRP20160389T1 (hr) | 2011-07-08 | 2016-04-15 | Derivati orvinola i tevinola korisni u liječenju bolesti ovisnosti o drogama i alkoholu |
Country Status (16)
| Country | Link |
|---|---|
| US (5) | US9051334B2 (hr) |
| EP (1) | EP2729469B1 (hr) |
| JP (2) | JP6117780B2 (hr) |
| CA (1) | CA2841169C (hr) |
| CY (1) | CY1117674T1 (hr) |
| DK (1) | DK2729469T3 (hr) |
| ES (1) | ES2572508T3 (hr) |
| GB (1) | GB201111775D0 (hr) |
| HK (1) | HK1198031A1 (hr) |
| HR (1) | HRP20160389T1 (hr) |
| HU (1) | HUE028785T2 (hr) |
| PL (1) | PL2729469T3 (hr) |
| RS (1) | RS54830B1 (hr) |
| SI (1) | SI2729469T1 (hr) |
| SM (1) | SMT201600154B (hr) |
| WO (1) | WO2013007986A1 (hr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201111775D0 (en) | 2011-07-08 | 2011-08-24 | Univ Bath | Compounds and uses thereof |
| PT3321269T (pt) | 2011-10-03 | 2020-07-24 | Johnson Matthey Plc | Processo para preparar intermediários de buprenorfina |
| WO2015097548A1 (en) * | 2013-12-26 | 2015-07-02 | Purdue Pharma L.P. | 7-beta-alkyl analogs of orvinols |
| TW201607923A (zh) | 2014-07-15 | 2016-03-01 | 歌林達有限公司 | 被取代之氮螺環（４．５）癸烷衍生物 |
| GB201716830D0 (en) | 2017-10-13 | 2017-11-29 | Cambrex Charles City Inc | New Process |
| CN110117288A (zh) * | 2018-02-07 | 2019-08-13 | 复旦大学 | 7β-甲基-奈培酮衍生物及其制备方法和用途 |
| CN114195798B (zh) * | 2021-12-31 | 2023-07-28 | 复旦大学 | 7α-甲基稠环吗啡类衍生物及其制备方法和用途 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3474101A (en) | 1960-09-05 | 1969-10-21 | Reckitt & Sons Ltd | Thebaine and oripavine derivatives |
| GB1136214A (en) | 1965-06-15 | 1968-12-11 | Reckitt & Sons Ltd | Thebaine and oripavine derivatives |
| GB937214A (en) | 1961-06-02 | 1963-09-18 | J F Macfarlan & Company Ltd | Oripavine derivatives |
| GB925723A (en) | 1960-09-05 | 1963-05-08 | J F Macfarlan & Company Ltd | Novel thebaine derivatives |
| GB902659A (en) | 1961-02-02 | 1962-08-09 | J F Macfarlan & Company Ltd | A process for the production of a derivative of thebaine |
| NL289751A (hr) | 1962-03-02 | |||
| DE1493696A1 (de) | 1965-02-17 | 1969-12-18 | Hoechst Ag | Verfahren zur Herstellung klarfluessiger,leicht mit Wasser verduennbarer Fettsaeurekondensationsprodukte |
| WO2004078178A1 (en) | 2003-03-03 | 2004-09-16 | Markus Heilig | Buprenorphine compounds for treatment of alcohol dependence and excessive alcohol use |
| GB201111775D0 (en) * | 2011-07-08 | 2011-08-24 | Univ Bath | Compounds and uses thereof |
-
2011
- 2011-07-08 GB GBGB1111775.1A patent/GB201111775D0/en not_active Ceased
-
2012
- 2012-07-05 JP JP2014519623A patent/JP6117780B2/ja active Active
- 2012-07-05 ES ES12735607T patent/ES2572508T3/es active Active
- 2012-07-05 RS RS20160426A patent/RS54830B1/sr unknown
- 2012-07-05 EP EP12735607.9A patent/EP2729469B1/en active Active
- 2012-07-05 DK DK12735607.9T patent/DK2729469T3/en active
- 2012-07-05 SI SI201230514A patent/SI2729469T1/sl unknown
- 2012-07-05 CA CA2841169A patent/CA2841169C/en active Active
- 2012-07-05 US US14/131,361 patent/US9051334B2/en active Active
- 2012-07-05 HU HUE12735607A patent/HUE028785T2/en unknown
- 2012-07-05 PL PL12735607.9T patent/PL2729469T3/pl unknown
- 2012-07-05 WO PCT/GB2012/051575 patent/WO2013007986A1/en active Application Filing
-
2014
- 2014-11-14 HK HK14111535.3A patent/HK1198031A1/zh not_active IP Right Cessation
-
2015
- 2015-03-31 US US14/674,578 patent/US9259422B2/en active Active
- 2015-07-06 JP JP2015135460A patent/JP6117862B2/ja active Active
-
2016
- 2016-01-20 US US15/001,553 patent/US9480684B2/en active Active
- 2016-04-15 HR HRP20160389TT patent/HRP20160389T1/hr unknown
- 2016-05-31 SM SM201600154T patent/SMT201600154B/it unknown
- 2016-06-21 CY CY20161100558T patent/CY1117674T1/el unknown
- 2016-10-27 US US15/336,193 patent/US9890170B2/en active Active
-
2017
- 2017-10-03 US US15/723,871 patent/US10030031B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| ES2572508T3 (es) | 2016-05-31 |
| US10030031B2 (en) | 2018-07-24 |
| JP2015172089A (ja) | 2015-10-01 |
| EP2729469B1 (en) | 2016-03-30 |
| US20140213603A1 (en) | 2014-07-31 |
| EP2729469A1 (en) | 2014-05-14 |
| RS54830B1 (sr) | 2016-10-31 |
| DK2729469T3 (en) | 2016-07-18 |
| US20170044173A1 (en) | 2017-02-16 |
| HUE028785T2 (en) | 2017-01-30 |
| CY1117674T1 (el) | 2017-05-17 |
| WO2013007986A1 (en) | 2013-01-17 |
| US9480684B2 (en) | 2016-11-01 |
| PL2729469T3 (pl) | 2016-09-30 |
| JP2014522854A (ja) | 2014-09-08 |
| GB201111775D0 (en) | 2011-08-24 |
| CA2841169A1 (en) | 2013-01-17 |
| US9890170B2 (en) | 2018-02-13 |
| US20160136151A1 (en) | 2016-05-19 |
| SMT201600154B (it) | 2016-08-31 |
| SI2729469T1 (sl) | 2016-07-29 |
| JP6117862B2 (ja) | 2017-04-19 |
| HK1198031A1 (zh) | 2015-03-06 |
| JP6117780B2 (ja) | 2017-04-19 |
| US9051334B2 (en) | 2015-06-09 |
| US20150202200A1 (en) | 2015-07-23 |
| US20180030062A1 (en) | 2018-02-01 |
| US9259422B2 (en) | 2016-02-16 |
| CA2841169C (en) | 2019-08-27 |
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