RU2013142364A - Замещенные производные 6,7-диалкокси-3-изохинолинола в качестве ингибиторов фосфодиэстеразы 10 (фдэ10а) - Google Patents
Замещенные производные 6,7-диалкокси-3-изохинолинола в качестве ингибиторов фосфодиэстеразы 10 (фдэ10а) Download PDFInfo
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- RU2013142364A RU2013142364A RU2013142364/04A RU2013142364A RU2013142364A RU 2013142364 A RU2013142364 A RU 2013142364A RU 2013142364/04 A RU2013142364/04 A RU 2013142364/04A RU 2013142364 A RU2013142364 A RU 2013142364A RU 2013142364 A RU2013142364 A RU 2013142364A
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- methyl
- dimethoxy
- dihydrochloride
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- 239000003112 inhibitor Substances 0.000 title 1
- -1 azido, hydroxy Chemical group 0.000 claims abstract 22
- 150000001875 compounds Chemical class 0.000 claims abstract 17
- 125000001424 substituent group Chemical group 0.000 claims abstract 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 10
- 125000003118 aryl group Chemical group 0.000 claims abstract 9
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 8
- 150000003839 salts Chemical class 0.000 claims abstract 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 6
- 125000005843 halogen group Chemical group 0.000 claims abstract 5
- 125000004104 aryloxy group Chemical group 0.000 claims abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000004171 alkoxy aryl group Chemical group 0.000 claims abstract 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract 3
- 125000004429 atom Chemical group 0.000 claims abstract 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 3
- 239000001257 hydrogen Substances 0.000 claims abstract 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims abstract 2
- 125000003277 amino group Chemical group 0.000 claims abstract 2
- 229910052799 carbon Inorganic materials 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 2
- 229910052736 halogen Inorganic materials 0.000 claims abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract 2
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 6
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- GQSXXDNIECLFIW-UHFFFAOYSA-N 2H-isoquinolin-3-one dihydrochloride Chemical compound C1=CC2=CC(=O)NC=C2C=C1.Cl.Cl GQSXXDNIECLFIW-UHFFFAOYSA-N 0.000 claims 3
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- 231100000566 intoxication Toxicity 0.000 claims 3
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- 239000002581 neurotoxin Substances 0.000 claims 3
- 231100000618 neurotoxin Toxicity 0.000 claims 3
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- 229940005483 opioid analgesics Drugs 0.000 claims 3
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 claims 3
- 229950010883 phencyclidine Drugs 0.000 claims 3
- 231100000572 poisoning Toxicity 0.000 claims 3
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
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- BTSKXFMPMDCFCA-UHFFFAOYSA-N 1-ethyl-4-[[2-(ethylamino)-7-fluoro-6-methoxyquinolin-3-yl]methyl]-6,7-dimethoxy-2h-isoquinolin-3-one;dihydrochloride Chemical compound Cl.Cl.COC1=C(OC)C=C2C(CC3=CC4=CC(OC)=C(F)C=C4N=C3NCC)=C(O)N=C(CC)C2=C1 BTSKXFMPMDCFCA-UHFFFAOYSA-N 0.000 claims 1
- BGTMPYLBFUAQHC-UHFFFAOYSA-N 1-ethyl-6,7-dimethoxy-4-(naphthalen-2-ylmethyl)-2h-isoquinolin-3-one;hydrochloride Chemical compound Cl.C12=CC(OC)=C(OC)C=C2C(CC)=NC(O)=C1CC1=CC=C(C=CC=C2)C2=C1 BGTMPYLBFUAQHC-UHFFFAOYSA-N 0.000 claims 1
- DJJPQDXBFFRDNN-UHFFFAOYSA-N 1-ethyl-6,7-dimethoxy-4-(quinolin-3-ylmethyl)-2h-isoquinolin-3-one;dihydrochloride Chemical compound Cl.Cl.C12=CC(OC)=C(OC)C=C2C(CC)=NC(O)=C1CC1=CN=C(C=CC=C2)C2=C1 DJJPQDXBFFRDNN-UHFFFAOYSA-N 0.000 claims 1
- VBYLUENSVNFKPN-UHFFFAOYSA-N 1-ethyl-6,7-dimethoxy-4-[(2-methylquinolin-6-yl)methyl]-2h-isoquinolin-3-one;dihydrochloride Chemical compound Cl.Cl.C12=CC(OC)=C(OC)C=C2C(CC)=NC(O)=C1CC1=CC=C(N=C(C)C=C2)C2=C1 VBYLUENSVNFKPN-UHFFFAOYSA-N 0.000 claims 1
- ADIJDXVEENNLQW-UHFFFAOYSA-N 1-ethyl-6,7-dimethoxy-4-[(3-phenylphenyl)methyl]-2h-isoquinolin-3-one;hydrochloride Chemical compound Cl.C12=CC(OC)=C(OC)C=C2C(CC)=NC(O)=C1CC(C=1)=CC=CC=1C1=CC=CC=C1 ADIJDXVEENNLQW-UHFFFAOYSA-N 0.000 claims 1
- HTODCQDAVFLCGE-UHFFFAOYSA-N 1-ethyl-6,7-dimethoxy-4-[(6-methoxyquinolin-3-yl)methyl]-2h-isoquinolin-3-one;dihydrochloride Chemical compound Cl.Cl.C12=CC(OC)=C(OC)C=C2C(CC)=NC(O)=C1CC1=CN=C(C=CC(OC)=C2)C2=C1 HTODCQDAVFLCGE-UHFFFAOYSA-N 0.000 claims 1
- PLNFMLXCFNHUGV-UHFFFAOYSA-N 1-ethyl-6,7-dimethoxy-4-[(7-methoxyquinolin-3-yl)methyl]-2h-isoquinolin-3-one;dihydrochloride Chemical compound Cl.Cl.C12=CC(OC)=C(OC)C=C2C(CC)=NC(O)=C1CC1=CN=C(C=C(OC)C=C2)C2=C1 PLNFMLXCFNHUGV-UHFFFAOYSA-N 0.000 claims 1
- OONPRRFULQGCFN-UHFFFAOYSA-N 1-ethyl-6,7-dimethoxy-4-[[3-(4-methoxyphenyl)phenyl]methyl]-2h-isoquinolin-3-one;hydrochloride Chemical compound Cl.C12=CC(OC)=C(OC)C=C2C(CC)=NC(O)=C1CC(C=1)=CC=CC=1C1=CC=C(OC)C=C1 OONPRRFULQGCFN-UHFFFAOYSA-N 0.000 claims 1
- NOIJZVSXLMQEJL-UHFFFAOYSA-N 1-ethyl-6,7-dimethoxy-4-[[6-(methylamino)-[1,3]dioxolo[4,5-g]quinolin-7-yl]methyl]-2h-isoquinolin-3-one;dihydrochloride Chemical compound Cl.Cl.C12=CC(OC)=C(OC)C=C2C(CC)=NC(O)=C1CC(C(=NC1=C2)NC)=CC1=CC1=C2OCO1 NOIJZVSXLMQEJL-UHFFFAOYSA-N 0.000 claims 1
- IEQURDALEIJEIX-UHFFFAOYSA-N 1-ethyl-6,7-dimethoxy-4-[[6-methoxy-2-(2-methoxyethylamino)quinolin-3-yl]methyl]-2h-isoquinolin-3-one;dihydrochloride Chemical compound Cl.Cl.C12=CC(OC)=C(OC)C=C2C(CC)=NC(O)=C1CC1=CC2=CC(OC)=CC=C2N=C1NCCOC IEQURDALEIJEIX-UHFFFAOYSA-N 0.000 claims 1
- HKWJSECIAGWHAV-UHFFFAOYSA-N 1-ethyl-6,7-dimethoxy-4-[[6-methoxy-2-(methylamino)quinolin-3-yl]methyl]-2h-isoquinolin-3-one Chemical compound C12=CC(OC)=C(OC)C=C2C(CC)=NC(O)=C1CC1=CC2=CC(OC)=CC=C2N=C1NC HKWJSECIAGWHAV-UHFFFAOYSA-N 0.000 claims 1
- FQRJDTOPZUNTSF-UHFFFAOYSA-N 1-ethyl-6,7-dimethoxy-4-[[6-methoxy-2-(propan-2-ylamino)quinolin-3-yl]methyl]-2h-isoquinolin-3-one;dihydrochloride Chemical compound Cl.Cl.C12=CC(OC)=C(OC)C=C2C(CC)=NC(O)=C1CC1=CC2=CC(OC)=CC=C2N=C1NC(C)C FQRJDTOPZUNTSF-UHFFFAOYSA-N 0.000 claims 1
- FBANUZRHSYFYSB-UHFFFAOYSA-N 1-ethyl-6,7-dimethoxy-4-[[6-methoxy-2-(propylamino)quinolin-3-yl]methyl]-2h-isoquinolin-3-one;dihydrochloride Chemical compound Cl.Cl.COC1=C(OC)C=C2C(CC3=CC4=CC(OC)=CC=C4N=C3NCCC)=C(O)N=C(CC)C2=C1 FBANUZRHSYFYSB-UHFFFAOYSA-N 0.000 claims 1
- HFVNDVLCVJBYIK-UHFFFAOYSA-N 3,6,7-trimethoxy-1-methyl-4-(naphthalen-2-ylmethyl)isoquinoline;hydrochloride Chemical compound Cl.C1=CC=CC2=CC(CC=3C(OC)=NC(C)=C4C=C(C(=CC4=3)OC)OC)=CC=C21 HFVNDVLCVJBYIK-UHFFFAOYSA-N 0.000 claims 1
- BSLRKZKLHQQATI-UHFFFAOYSA-N 4-(dibenzofuran-2-ylmethyl)-1-ethyl-6,7-dimethoxy-2h-isoquinolin-3-one;hydrochloride Chemical compound Cl.C12=CC(OC)=C(OC)C=C2C(CC)=NC(O)=C1CC1=CC=C(OC=2C3=CC=CC=2)C3=C1 BSLRKZKLHQQATI-UHFFFAOYSA-N 0.000 claims 1
- FNMCICHSSNPOEH-UHFFFAOYSA-N 4-(dibenzofuran-2-ylmethyl)-6,7-dimethoxy-1-propyl-2h-isoquinolin-3-one;hydrochloride Chemical compound Cl.C12=CC(OC)=C(OC)C=C2C(CCC)=NC(O)=C1CC1=CC=C(OC=2C3=CC=CC=2)C3=C1 FNMCICHSSNPOEH-UHFFFAOYSA-N 0.000 claims 1
- CTOHHRUHXXPTIZ-UHFFFAOYSA-N 4-(dibenzofuran-2-ylmethyl)-6,7-dimethoxy-1-propylisoquinolin-3-amine;hydrochloride Chemical compound Cl.C12=CC(OC)=C(OC)C=C2C(CCC)=NC(N)=C1CC1=CC=C(OC=2C3=CC=CC=2)C3=C1 CTOHHRUHXXPTIZ-UHFFFAOYSA-N 0.000 claims 1
- FMSANJIVZDRHEG-UHFFFAOYSA-N 4-(isoquinolin-5-ylmethyl)-6,7-dimethoxy-1-methyl-2h-isoquinolin-3-one Chemical compound N1=CC=C2C(CC=3C(O)=NC(C)=C4C=C(C(=CC4=3)OC)OC)=CC=CC2=C1 FMSANJIVZDRHEG-UHFFFAOYSA-N 0.000 claims 1
- DVDXVRDJQQVUQP-UHFFFAOYSA-N 4-(isoquinolin-6-ylmethyl)-6,7-dimethoxy-1-methyl-2h-isoquinolin-3-one;dihydrochloride Chemical compound Cl.Cl.C1=NC=CC2=CC(CC=3C(O)=NC(C)=C4C=C(C(=CC4=3)OC)OC)=CC=C21 DVDXVRDJQQVUQP-UHFFFAOYSA-N 0.000 claims 1
- OSTDSZLKWVKGAL-UHFFFAOYSA-N 4-[(2-azido-6-methoxyquinolin-3-yl)methyl]-1-ethyl-6,7-dimethoxy-2h-isoquinolin-3-one;dihydrochloride Chemical compound Cl.Cl.C12=CC(OC)=C(OC)C=C2C(CC)=NC(O)=C1CC1=CC2=CC(OC)=CC=C2N=C1N=[N+]=[N-] OSTDSZLKWVKGAL-UHFFFAOYSA-N 0.000 claims 1
- LINJDHXBERWBQA-UHFFFAOYSA-N 4-[(2-butyl-6-methoxyquinolin-3-yl)methyl]-6,7-dimethoxy-1-propyl-2h-isoquinolin-3-one;dihydrochloride Chemical compound Cl.Cl.COC1=C(OC)C=C2C(CC3=CC4=CC(OC)=CC=C4N=C3CCCC)=C(O)N=C(CCC)C2=C1 LINJDHXBERWBQA-UHFFFAOYSA-N 0.000 claims 1
- XTYBJTMZTAVKPZ-UHFFFAOYSA-N 4-[(2-ethyl-6-methoxyquinolin-3-yl)methyl]-6,7-dimethoxy-1-propyl-2h-isoquinolin-3-one;dihydrochloride Chemical compound Cl.Cl.C12=CC(OC)=C(OC)C=C2C(CCC)=NC(O)=C1CC1=CC2=CC(OC)=CC=C2N=C1CC XTYBJTMZTAVKPZ-UHFFFAOYSA-N 0.000 claims 1
- SZVUGARWWCBPPS-UHFFFAOYSA-N 4-[(3,4-dimethoxyphenyl)methyl]-3,6,7-trimethoxy-1-methylisoquinoline;hydrochloride Chemical compound Cl.C1=C(OC)C(OC)=CC=C1CC1=C(OC)N=C(C)C2=CC(OC)=C(OC)C=C12 SZVUGARWWCBPPS-UHFFFAOYSA-N 0.000 claims 1
- ZMXLGFVWEKNIFA-UHFFFAOYSA-N 4-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-1-methyl-2h-isoquinolin-3-one;hydrochloride Chemical compound Cl.C1=C(OC)C(OC)=CC=C1CC1=C(O)N=C(C)C2=CC(OC)=C(OC)C=C12 ZMXLGFVWEKNIFA-UHFFFAOYSA-N 0.000 claims 1
- KAGDIIFYXXVWJH-UHFFFAOYSA-N 4-[2-(ethylamino)-6-methoxyquinoline-3-carbonyl]-6,7-dimethoxy-1-methyl-2h-isoquinolin-3-one;dihydrochloride Chemical compound Cl.Cl.COC1=C(OC)C=C2C(C(=O)C3=CC4=CC(OC)=CC=C4N=C3NCC)=C(O)N=C(C)C2=C1 KAGDIIFYXXVWJH-UHFFFAOYSA-N 0.000 claims 1
- FGFCTKRLUAPAEZ-UHFFFAOYSA-N 4-[[2-(benzylamino)-6-methoxyquinolin-3-yl]methyl]-1-ethyl-6,7-dimethoxy-2h-isoquinolin-3-one;dihydrochloride Chemical compound Cl.Cl.C12=CC(OC)=C(OC)C=C2C(CC)=NC(O)=C1CC1=CC2=CC(OC)=CC=C2N=C1NCC1=CC=CC=C1 FGFCTKRLUAPAEZ-UHFFFAOYSA-N 0.000 claims 1
- ZDCFYQHSRMELKU-UHFFFAOYSA-N 4-[[2-(dimethylamino)-6-methylquinolin-3-yl]methyl]-6,7-dimethoxy-1-propyl-2h-isoquinolin-3-one;dihydrochloride Chemical compound Cl.Cl.C12=CC(OC)=C(OC)C=C2C(CCC)=NC(O)=C1CC1=CC2=CC(C)=CC=C2N=C1N(C)C ZDCFYQHSRMELKU-UHFFFAOYSA-N 0.000 claims 1
- YXQJQBZCXNFOKH-UHFFFAOYSA-N 4-[[2-(ethylamino)-6-methoxyquinolin-3-yl]methyl]-6,7-dimethoxy-1-(methoxymethyl)-2h-isoquinolin-3-one;dihydrochloride Chemical compound Cl.Cl.COC1=C(OC)C=C2C(CC3=CC4=CC(OC)=CC=C4N=C3NCC)=C(O)N=C(COC)C2=C1 YXQJQBZCXNFOKH-UHFFFAOYSA-N 0.000 claims 1
- BYNAPGZGYUBTOW-UHFFFAOYSA-N 4-[[2-(ethylamino)-6-methoxyquinolin-3-yl]methyl]-6,7-dimethoxy-1-propan-2-yl-2h-isoquinolin-3-one;dihydrochloride Chemical compound Cl.Cl.COC1=C(OC)C=C2C(CC3=CC4=CC(OC)=CC=C4N=C3NCC)=C(O)N=C(C(C)C)C2=C1 BYNAPGZGYUBTOW-UHFFFAOYSA-N 0.000 claims 1
- JHIDGKNWYWURNG-UHFFFAOYSA-N 4-[[2-(ethylamino)-6-methylquinolin-3-yl]methyl]-6,7-dimethoxy-1-propyl-2h-isoquinolin-3-one;dihydrochloride Chemical compound Cl.Cl.C12=CC(OC)=C(OC)C=C2C(CCC)=NC(O)=C1CC1=CC2=CC(C)=CC=C2N=C1NCC JHIDGKNWYWURNG-UHFFFAOYSA-N 0.000 claims 1
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- XBCIZFMCIKUBPM-UHFFFAOYSA-N 4-[[3-(3-aminophenyl)phenyl]methyl]-1-ethyl-6,7-dimethoxy-2h-isoquinolin-3-one;dihydrochloride Chemical compound Cl.Cl.C12=CC(OC)=C(OC)C=C2C(CC)=NC(O)=C1CC(C=1)=CC=CC=1C1=CC=CC(N)=C1 XBCIZFMCIKUBPM-UHFFFAOYSA-N 0.000 claims 1
- SWBCIDGZDZCQKC-UHFFFAOYSA-N 4-[[6,7-dihydroxy-2-(methylamino)quinolin-3-yl]methyl]-6,7-dimethoxy-1-methyl-2H-isoquinolin-3-one dihydrochloride Chemical compound Cl.Cl.COC1=C(OC)C=C2C(CC3=CC4=CC(O)=C(O)C=C4N=C3NC)=C(O)N=C(C)C2=C1 SWBCIDGZDZCQKC-UHFFFAOYSA-N 0.000 claims 1
- KUCSXSVAROGQCH-UHFFFAOYSA-N 4-[[6-(dimethylamino)-[1,3]dioxolo[4,5-g]quinolin-7-yl]methyl]-6,7-dimethoxy-1-propyl-2h-isoquinolin-3-one;dihydrochloride Chemical compound Cl.Cl.C12=CC(OC)=C(OC)C=C2C(CCC)=NC(O)=C1CC(C(=NC1=C2)N(C)C)=CC1=CC1=C2OCO1 KUCSXSVAROGQCH-UHFFFAOYSA-N 0.000 claims 1
- VGFOROIFWFIFDX-UHFFFAOYSA-N 4-[[6-(ethylamino)-[1,3]dioxolo[4,5-g]quinolin-7-yl]methyl]-6,7-dimethoxy-1-propyl-2h-isoquinolin-3-one;dihydrochloride Chemical compound Cl.Cl.C12=CC(OC)=C(OC)C=C2C(CCC)=NC(O)=C1CC(C(=NC1=C2)NCC)=CC1=CC1=C2OCO1 VGFOROIFWFIFDX-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- 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
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
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-
2012
- 2012-02-17 CA CA2827724A patent/CA2827724A1/en not_active Abandoned
- 2012-02-17 RU RU2013142364/04A patent/RU2013142364A/ru not_active Application Discontinuation
- 2012-02-17 US US13/399,351 patent/US8772316B2/en active Active
- 2012-02-17 EP EP12706983.9A patent/EP2675791B1/en active Active
- 2012-02-17 WO PCT/US2012/025731 patent/WO2012112946A1/en not_active Ceased
- 2012-02-17 BR BR112013021180A patent/BR112013021180A2/pt not_active IP Right Cessation
- 2012-02-17 SG SG2013062807A patent/SG192839A1/en unknown
- 2012-02-17 MX MX2013009575A patent/MX2013009575A/es not_active Application Discontinuation
- 2012-02-17 AU AU2012219316A patent/AU2012219316A1/en not_active Abandoned
- 2012-02-17 CN CN2012800184663A patent/CN103476757A/zh active Pending
- 2012-02-17 JP JP2013554657A patent/JP2014510055A/ja active Pending
- 2012-02-17 KR KR1020137024525A patent/KR20140009372A/ko not_active Withdrawn
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2013
- 2013-08-18 IL IL228008A patent/IL228008A0/en unknown
- 2013-08-19 CL CL2013002394A patent/CL2013002394A1/es unknown
- 2013-08-26 ZA ZA2013/06416A patent/ZA201306416B/en unknown
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2014
- 2014-06-25 US US14/314,930 patent/US9670181B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US20140309253A1 (en) | 2014-10-16 |
| ZA201306416B (en) | 2014-04-30 |
| SG192839A1 (en) | 2013-09-30 |
| CN103476757A (zh) | 2013-12-25 |
| MX2013009575A (es) | 2014-10-14 |
| CL2013002394A1 (es) | 2014-07-04 |
| KR20140009372A (ko) | 2014-01-22 |
| IL228008A0 (en) | 2013-09-30 |
| US20120214837A1 (en) | 2012-08-23 |
| AU2012219316A1 (en) | 2013-10-03 |
| JP2014510055A (ja) | 2014-04-24 |
| CA2827724A1 (en) | 2012-08-23 |
| WO2012112946A1 (en) | 2012-08-23 |
| EP2675791A1 (en) | 2013-12-25 |
| EP2675791B1 (en) | 2016-02-17 |
| US9670181B2 (en) | 2017-06-06 |
| BR112013021180A2 (pt) | 2019-09-24 |
| US8772316B2 (en) | 2014-07-08 |
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