JP2013523884A5 - - Google Patents
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- Publication number
- JP2013523884A5 JP2013523884A5 JP2013504972A JP2013504972A JP2013523884A5 JP 2013523884 A5 JP2013523884 A5 JP 2013523884A5 JP 2013504972 A JP2013504972 A JP 2013504972A JP 2013504972 A JP2013504972 A JP 2013504972A JP 2013523884 A5 JP2013523884 A5 JP 2013523884A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazol
- alkyl
- imidazo
- pyrimidin
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
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- 125000000217 alkyl group Chemical group 0.000 claims description 365
- 150000001875 compounds Chemical class 0.000 claims description 191
- 125000001424 substituent group Chemical group 0.000 claims description 71
- 150000003839 salts Chemical class 0.000 claims description 67
- 239000012453 solvate Substances 0.000 claims description 66
- -1 pyridinonyl Chemical group 0.000 claims description 63
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 59
- 125000004432 carbon atom Chemical group C* 0.000 claims description 47
- 229910052799 carbon Inorganic materials 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- 239000001257 hydrogen Substances 0.000 claims description 41
- 125000001153 fluoro group Chemical group F* 0.000 claims description 34
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims description 33
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000000304 alkynyl group Chemical group 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 230000008878 coupling Effects 0.000 claims description 18
- 238000010168 coupling process Methods 0.000 claims description 18
- 238000005859 coupling reaction Methods 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 10
- 241000124008 Mammalia Species 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 8
- 125000002619 bicyclic group Chemical group 0.000 claims description 8
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
- 125000003566 oxetanyl group Chemical group 0.000 claims description 8
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 6
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 238000002560 therapeutic procedure Methods 0.000 claims description 5
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 4
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 239000012025 fluorinating agent Substances 0.000 claims description 4
- 239000003446 ligand Substances 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims description 3
- 125000005605 benzo group Chemical group 0.000 claims description 3
- 125000004193 piperazinyl group Chemical group 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 claims description 2
- FHBAQURBTKEYHG-UHFFFAOYSA-N 2-[1-cyclopropylsulfonyl-3-[3-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrrol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(C=C2)C2(CC#N)CN(C2)S(=O)(=O)C2CC2)=N1 FHBAQURBTKEYHG-UHFFFAOYSA-N 0.000 claims description 2
- KLNXUTSCUIBQGB-UHFFFAOYSA-N 2-bromo-2-fluoroacetaldehyde Chemical compound FC(Br)C=O KLNXUTSCUIBQGB-UHFFFAOYSA-N 0.000 claims description 2
- AVAHZUUYBFUOPN-UHFFFAOYSA-N 2-chloro-2-fluoroacetaldehyde Chemical compound FC(Cl)C=O AVAHZUUYBFUOPN-UHFFFAOYSA-N 0.000 claims description 2
- QSKPIOLLBIHNAC-UHFFFAOYSA-N 2-chloro-acetaldehyde Chemical compound ClCC=O QSKPIOLLBIHNAC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 2
- 208000023275 Autoimmune disease Diseases 0.000 claims description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Chemical class CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 150000004791 alkyl magnesium halides Chemical class 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 208000037979 autoimmune inflammatory disease Diseases 0.000 claims description 2
- 125000002393 azetidinyl group Chemical group 0.000 claims description 2
- 125000006380 bromopyridyl group Chemical group 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 2
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 claims description 2
- 239000007822 coupling agent Substances 0.000 claims description 2
- 239000012024 dehydrating agents Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 210000000056 organ Anatomy 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 238000002054 transplantation Methods 0.000 claims description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 12
- 239000000203 mixture Substances 0.000 claims 6
- CDGWLOBEPYFSQW-UHFFFAOYSA-N 3-cyclopentyl-3-[4-[7-(4-morpholin-4-ylphenyl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=C(C=2N3C=CN=C3C=C(N=2)C=2C=CC(=CC=2)N2CCOCC2)C=NN1C(CC#N)C1CCCC1 CDGWLOBEPYFSQW-UHFFFAOYSA-N 0.000 claims 3
- PMKAQVQNDAXKOW-UHFFFAOYSA-N 3-cyclopentyl-3-[4-[7-[4-(1-methylpiperidin-4-yl)phenyl]imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1CN(C)CCC1C1=CC=C(C=2N=C(N3C=CN=C3C=2)C2=CN(N=C2)C(CC#N)C2CCCC2)C=C1 PMKAQVQNDAXKOW-UHFFFAOYSA-N 0.000 claims 3
- YUPDWXZOLVVALZ-UHFFFAOYSA-N 3-cyclopropyl-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C(CC#N)C2CC2)=N1 YUPDWXZOLVVALZ-UHFFFAOYSA-N 0.000 claims 3
- GEYUNVRSROHFKM-UHFFFAOYSA-N 3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]pentanedinitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C(CC#N)CC#N)=N1 GEYUNVRSROHFKM-UHFFFAOYSA-N 0.000 claims 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 2
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims 2
- ABNBEHYCFTZPKW-GDBMZVCRSA-N (3r)-3-[(1r)-2,2-difluorocyclopropyl]-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)[C@H](CC#N)[C@@H]2C(C2)(F)F)=N1 ABNBEHYCFTZPKW-GDBMZVCRSA-N 0.000 claims 1
- ABNBEHYCFTZPKW-GOEBONIOSA-N (3r)-3-[(1s)-2,2-difluorocyclopropyl]-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)[C@H](CC#N)[C@H]2C(C2)(F)F)=N1 ABNBEHYCFTZPKW-GOEBONIOSA-N 0.000 claims 1
- ABNBEHYCFTZPKW-HOCLYGCPSA-N (3s)-3-[(1s)-2,2-difluorocyclopropyl]-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)[C@@H](CC#N)[C@H]2C(C2)(F)F)=N1 ABNBEHYCFTZPKW-HOCLYGCPSA-N 0.000 claims 1
- 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 claims 1
- STHHLVCQSLRQNI-UHFFFAOYSA-N 1-azabicyclo[3.2.1]octane Chemical compound C1C2CCN1CCC2 STHHLVCQSLRQNI-UHFFFAOYSA-N 0.000 claims 1
- BVXLHMZUEHXJBO-UHFFFAOYSA-N 2-[1-(1,3-difluoropropan-2-yl)-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CN(C2)C(CF)CF)=N1 BVXLHMZUEHXJBO-UHFFFAOYSA-N 0.000 claims 1
- RRXZOVJYCGCGPH-UHFFFAOYSA-N 2-[1-(2,2-difluoroethyl)-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CN(CC(F)F)C2)=N1 RRXZOVJYCGCGPH-UHFFFAOYSA-N 0.000 claims 1
- XMUCZZPNAALHEK-UHFFFAOYSA-N 2-[1-(2-fluoroethyl)-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CN(CCF)C2)=N1 XMUCZZPNAALHEK-UHFFFAOYSA-N 0.000 claims 1
- UVPTWQHOIAUESY-UHFFFAOYSA-N 2-[1-(2-methylpropyl)-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1N(CC(C)C)CC1(CC#N)N1N=CC(C=2N3C=CN=C3C=C(N=2)C2=CN(C)N=C2)=C1 UVPTWQHOIAUESY-UHFFFAOYSA-N 0.000 claims 1
- WSXKODFFQDPKQQ-UHFFFAOYSA-N 2-[1-(3-fluoropropyl)-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CN(CCCF)C2)=N1 WSXKODFFQDPKQQ-UHFFFAOYSA-N 0.000 claims 1
- LIZHKRHZDLAJCN-UHFFFAOYSA-N 2-[1-(benzenesulfonyl)-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CN(C2)S(=O)(=O)C=2C=CC=CC=2)=N1 LIZHKRHZDLAJCN-UHFFFAOYSA-N 0.000 claims 1
- IXDYSBQNTZFBQM-UHFFFAOYSA-N 2-[1-(cyanomethyl)-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CN(CC#N)C2)=N1 IXDYSBQNTZFBQM-UHFFFAOYSA-N 0.000 claims 1
- AHXUTYXPZLGWHS-UHFFFAOYSA-N 2-[1-(cyclobutylmethyl)-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CN(CC3CCC3)C2)=N1 AHXUTYXPZLGWHS-UHFFFAOYSA-N 0.000 claims 1
- NUHSETASQOIQEV-UHFFFAOYSA-N 2-[1-(cyclopropylmethyl)-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CN(CC3CC3)C2)=N1 NUHSETASQOIQEV-UHFFFAOYSA-N 0.000 claims 1
- MZRDVCTYXZXBCQ-UHFFFAOYSA-N 2-[1-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]cyclohexyl]acetonitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CCCCC2)=N1 MZRDVCTYXZXBCQ-UHFFFAOYSA-N 0.000 claims 1
- AXJNUSNMBMLDCE-UHFFFAOYSA-N 2-[1-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]cyclopentyl]acetonitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CCCC2)=N1 AXJNUSNMBMLDCE-UHFFFAOYSA-N 0.000 claims 1
- GRVGHRKEVBNTAR-UHFFFAOYSA-N 2-[1-acetyl-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1N(C(=O)C)CC1(CC#N)N1N=CC(C=2N3C=CN=C3C=C(N=2)C2=CN(C)N=C2)=C1 GRVGHRKEVBNTAR-UHFFFAOYSA-N 0.000 claims 1
- LYNKUIAJEDKUOU-UHFFFAOYSA-N 2-[1-acetyl-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]pyrrolidin-3-yl]acetonitrile Chemical compound C1N(C(=O)C)CCC1(CC#N)N1N=CC(C=2N3C=CN=C3C=C(N=2)C2=CN(C)N=C2)=C1 LYNKUIAJEDKUOU-UHFFFAOYSA-N 0.000 claims 1
- WIKHNPCHNOOJMO-UHFFFAOYSA-N 2-[1-but-2-ynyl-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1N(CC#CC)CC1(CC#N)N1N=CC(C=2N3C=CN=C3C=C(N=2)C2=CN(C)N=C2)=C1 WIKHNPCHNOOJMO-UHFFFAOYSA-N 0.000 claims 1
- AWVZDWQVTXEGAK-UHFFFAOYSA-N 2-[1-cyclohexylsulfonyl-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CN(C2)S(=O)(=O)C2CCCCC2)=N1 AWVZDWQVTXEGAK-UHFFFAOYSA-N 0.000 claims 1
- MEKZXNYRRWVDBH-UHFFFAOYSA-N 2-[1-cyclopropyl-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CN(C2)C2CC2)=N1 MEKZXNYRRWVDBH-UHFFFAOYSA-N 0.000 claims 1
- DTOPBQTXJVBHDA-UHFFFAOYSA-N 2-[1-cyclopropylsulfonyl-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CN(C2)S(=O)(=O)C2CC2)=N1 DTOPBQTXJVBHDA-UHFFFAOYSA-N 0.000 claims 1
- KVSNEJVQFAUGNO-UHFFFAOYSA-N 2-[1-cyclopropylsulfonyl-3-[4-[7-(2-methoxypyrimidin-5-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1=NC(OC)=NC=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CN(C2)S(=O)(=O)C2CC2)=N1 KVSNEJVQFAUGNO-UHFFFAOYSA-N 0.000 claims 1
- VRVAYYXJPPDRDE-UHFFFAOYSA-N 2-[1-cyclopropylsulfonyl-3-[4-[7-(2-methyl-1,3-thiazol-5-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound S1C(C)=NC=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CN(C2)S(=O)(=O)C2CC2)=N1 VRVAYYXJPPDRDE-UHFFFAOYSA-N 0.000 claims 1
- BVAOKWYKPDLRNN-UHFFFAOYSA-N 2-[1-cyclopropylsulfonyl-3-[4-[7-(4-methoxyphenyl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1=CC(OC)=CC=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CN(C2)S(=O)(=O)C2CC2)=N1 BVAOKWYKPDLRNN-UHFFFAOYSA-N 0.000 claims 1
- GDQAHRLJKRQHDZ-UHFFFAOYSA-N 2-[1-ethyl-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1N(CC)CC1(CC#N)N1N=CC(C=2N3C=CN=C3C=C(N=2)C2=CN(C)N=C2)=C1 GDQAHRLJKRQHDZ-UHFFFAOYSA-N 0.000 claims 1
- QTISHRMBUYAIPL-UHFFFAOYSA-N 2-[1-ethyl-4-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]piperidin-4-yl]acetonitrile Chemical compound C1CN(CC)CCC1(CC#N)N1N=CC(C=2N3C=CN=C3C=C(N=2)C2=CN(C)N=C2)=C1 QTISHRMBUYAIPL-UHFFFAOYSA-N 0.000 claims 1
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- DFWMDEUJRFPCJI-UHFFFAOYSA-N 2-[3-[4-[7-(4-methoxyphenyl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]-1-(trifluoromethylsulfonyl)azetidin-3-yl]acetonitrile Chemical compound C1=CC(OC)=CC=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CN(C2)S(=O)(=O)C(F)(F)F)=N1 DFWMDEUJRFPCJI-UHFFFAOYSA-N 0.000 claims 1
- IZRUVVZILHUJBC-UHFFFAOYSA-N 2-[3-[4-[7-[1-(oxetan-3-yl)pyrazol-4-yl]imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]-1-(2,2,2-trifluoroethyl)azetidin-3-yl]acetonitrile Chemical compound C1N(CC(F)(F)F)CC1(CC#N)N1N=CC(C=2N3C=CN=C3C=C(N=2)C2=CN(N=C2)C2COC2)=C1 IZRUVVZILHUJBC-UHFFFAOYSA-N 0.000 claims 1
- MYFUQDIKPISEBR-UHFFFAOYSA-N 2-[3-[4-[7-[1-(oxetan-3-yl)pyrazol-4-yl]imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]-1-(2,2,3,3,3-pentafluoropropyl)azetidin-3-yl]acetonitrile Chemical compound C1N(CC(F)(F)C(F)(F)F)CC1(CC#N)N1N=CC(C=2N3C=CN=C3C=C(N=2)C2=CN(N=C2)C2COC2)=C1 MYFUQDIKPISEBR-UHFFFAOYSA-N 0.000 claims 1
- NSOQJYLCMLVDSD-UHFFFAOYSA-N 2-[3-[4-[7-[4-(4-methylpiperazin-1-yl)phenyl]imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]-1-(2,2,2-trifluoroethyl)azetidin-3-yl]acetonitrile Chemical compound C1CN(C)CCN1C1=CC=C(C=2N=C(N3C=CN=C3C=2)C2=CN(N=C2)C2(CC#N)CN(CC(F)(F)F)C2)C=C1 NSOQJYLCMLVDSD-UHFFFAOYSA-N 0.000 claims 1
- HMZOXQBZHCFMOR-UHFFFAOYSA-N 2-[3-[4-[7-[4-(4-methylpiperazin-1-yl)phenyl]imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]-1-(trifluoromethylsulfonyl)azetidin-3-yl]acetonitrile Chemical compound C1CN(C)CCN1C1=CC=C(C=2N=C(N3C=CN=C3C=2)C2=CN(N=C2)C2(CC#N)CN(C2)S(=O)(=O)C(F)(F)F)C=C1 HMZOXQBZHCFMOR-UHFFFAOYSA-N 0.000 claims 1
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- KRKSMAMKUHJRAO-UHFFFAOYSA-N 3-(5-bromopyridin-3-yl)-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C(CC#N)C=2C=C(Br)C=NC=2)=N1 KRKSMAMKUHJRAO-UHFFFAOYSA-N 0.000 claims 1
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- AJPWDEWJGZFKES-UHFFFAOYSA-N 3-[4-[3-chloro-7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]-3-cyclopropylpropanenitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=C(Cl)N2C(C2=CN(N=C2)C(CC#N)C2CC2)=N1 AJPWDEWJGZFKES-UHFFFAOYSA-N 0.000 claims 1
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- UQFLUXXENJUNNR-UHFFFAOYSA-N 3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]-3-[3-(trifluoromethyl)phenyl]propanenitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C(CC#N)C=2C=C(C=CC=2)C(F)(F)F)=N1 UQFLUXXENJUNNR-UHFFFAOYSA-N 0.000 claims 1
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- QFKUHHHTOCDBBJ-UHFFFAOYSA-N 3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]-3-pyridin-2-ylpropanenitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C(CC#N)C=2N=CC=CC=2)=N1 QFKUHHHTOCDBBJ-UHFFFAOYSA-N 0.000 claims 1
- RARCFHGIWRCBSK-UHFFFAOYSA-N 3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]-3-pyridin-3-ylpropanenitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C(CC#N)C=2C=NC=CC=2)=N1 RARCFHGIWRCBSK-UHFFFAOYSA-N 0.000 claims 1
- OYSMCZSDTIWOJT-UHFFFAOYSA-N 3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]-3-pyridin-4-ylpropanenitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C(CC#N)C=2C=CN=CC=2)=N1 OYSMCZSDTIWOJT-UHFFFAOYSA-N 0.000 claims 1
- GXAMHDZDASSNKZ-UHFFFAOYSA-N 3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(CCC#N)N=C2)=N1 GXAMHDZDASSNKZ-UHFFFAOYSA-N 0.000 claims 1
- COIHEXKIXPEXTH-UHFFFAOYSA-N 3-[4-[7-(4-morpholin-4-ylphenyl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]butanenitrile Chemical compound C1=NN(C(CC#N)C)C=C1C1=NC(C=2C=CC(=CC=2)N2CCOCC2)=CC2=NC=CN12 COIHEXKIXPEXTH-UHFFFAOYSA-N 0.000 claims 1
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- CMQJUUYCKXJGGQ-UHFFFAOYSA-N 3-cyclobutyl-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C(CC#N)C2CCC2)=N1 CMQJUUYCKXJGGQ-UHFFFAOYSA-N 0.000 claims 1
- MHBLMJUJRRLINT-UHFFFAOYSA-N 3-cyclopentyl-3-[3-methyl-4-[7-(4-morpholin-4-ylphenyl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound CC1=NN(C(CC#N)C2CCCC2)C=C1C(N1C=CN=C1C=1)=NC=1C(C=C1)=CC=C1N1CCOCC1 MHBLMJUJRRLINT-UHFFFAOYSA-N 0.000 claims 1
- JMUWHIMQRSJDOC-UHFFFAOYSA-N 3-cyclopentyl-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C(CC#N)C2CCCC2)=N1 JMUWHIMQRSJDOC-UHFFFAOYSA-N 0.000 claims 1
- AKPSVTAHTDVPLQ-UHFFFAOYSA-N 3-cyclopropyl-3-[3-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=NN(C=C2)C(CC#N)C2CC2)=N1 AKPSVTAHTDVPLQ-UHFFFAOYSA-N 0.000 claims 1
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- VRPDPZTVSKSYRJ-UHFFFAOYSA-N 3-cyclopropyl-3-[4-[3-fluoro-7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=C(F)N2C(C2=CN(N=C2)C(CC#N)C2CC2)=N1 VRPDPZTVSKSYRJ-UHFFFAOYSA-N 0.000 claims 1
- DWAIHCDEWKZVTH-UHFFFAOYSA-N 3-cyclopropyl-3-[4-[7-(1,2,3,4-tetrahydroisoquinolin-6-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=C(C=2N3C=CN=C3C=C(N=2)C=2C=C3CCNCC3=CC=2)C=NN1C(CC#N)C1CC1 DWAIHCDEWKZVTH-UHFFFAOYSA-N 0.000 claims 1
- ZTKNHJIXJVXOBT-UHFFFAOYSA-N 3-cyclopropyl-3-[4-[7-(1,2,3,4-tetrahydroisoquinolin-7-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=C(C=2N3C=CN=C3C=C(N=2)C=2C=C3CNCCC3=CC=2)C=NN1C(CC#N)C1CC1 ZTKNHJIXJVXOBT-UHFFFAOYSA-N 0.000 claims 1
- VLWHWRQGLKVENE-UHFFFAOYSA-N 3-cyclopropyl-3-[4-[7-(1,3-oxazol-5-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=C(C=2N3C=CN=C3C=C(N=2)C=2OC=NC=2)C=NN1C(CC#N)C1CC1 VLWHWRQGLKVENE-UHFFFAOYSA-N 0.000 claims 1
- LAFPPLQHGHUMHU-UHFFFAOYSA-N 3-cyclopropyl-3-[4-[7-(1,3-thiazol-5-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=C(C=2N3C=CN=C3C=C(N=2)C=2SC=NC=2)C=NN1C(CC#N)C1CC1 LAFPPLQHGHUMHU-UHFFFAOYSA-N 0.000 claims 1
- QLKWQBWEZHFRCD-UHFFFAOYSA-N 3-cyclopropyl-3-[4-[7-(1-ethylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=NN(CC)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C(CC#N)C2CC2)=N1 QLKWQBWEZHFRCD-UHFFFAOYSA-N 0.000 claims 1
- QPWQVIRMVCSPIJ-UHFFFAOYSA-N 3-cyclopropyl-3-[4-[7-(1-propan-2-ylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=NN(C(C)C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C(CC#N)C2CC2)=N1 QPWQVIRMVCSPIJ-UHFFFAOYSA-N 0.000 claims 1
- OLCSDVVNTNKXDO-UHFFFAOYSA-N 3-cyclopropyl-3-[4-[7-(1h-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=C(C=2N3C=CN=C3C=C(N=2)C2=CNN=C2)C=NN1C(CC#N)C1CC1 OLCSDVVNTNKXDO-UHFFFAOYSA-N 0.000 claims 1
- HMTOHHCQXJAJIR-UHFFFAOYSA-N 3-cyclopropyl-3-[4-[7-(2-methyl-1,3-thiazol-5-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound S1C(C)=NC=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C(CC#N)C2CC2)=N1 HMTOHHCQXJAJIR-UHFFFAOYSA-N 0.000 claims 1
- CIKUAIFCICQYFL-UHFFFAOYSA-N 3-cyclopropyl-3-[4-[7-(2-methyl-3,4-dihydro-1h-isoquinolin-6-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C=1C=C2CN(C)CCC2=CC=1C(N=1)=CC2=NC=CN2C=1C(=C1)C=NN1C(CC#N)C1CC1 CIKUAIFCICQYFL-UHFFFAOYSA-N 0.000 claims 1
- SYKYCBPRCKWSDD-UHFFFAOYSA-N 3-cyclopropyl-3-[4-[7-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=C2CN(C)CCC2=CC=C1C(N=1)=CC2=NC=CN2C=1C(=C1)C=NN1C(CC#N)C1CC1 SYKYCBPRCKWSDD-UHFFFAOYSA-N 0.000 claims 1
- KXIGBXQAKMNERW-UHFFFAOYSA-N 3-cyclopropyl-3-[4-[7-(2-methylpyridin-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=NC(C)=CC(C=2N=C(N3C=CN=C3C=2)C2=CN(N=C2)C(CC#N)C2CC2)=C1 KXIGBXQAKMNERW-UHFFFAOYSA-N 0.000 claims 1
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| EP2740731B1 (en) | 2007-06-13 | 2016-03-23 | Incyte Holdings Corporation | Crystalline salts of the janus kinase inhibitor (r)-3-(4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl)-3-cyclopentylpropanenitrile |
| NZ596479A (en) | 2009-05-22 | 2014-01-31 | Incyte Corp | N-(hetero)aryl-pyrrolidine derivatives of pyrazol-4-yl-pyrrolo[2,3-d]pyrimidines and pyrrol-3-yl-pyrrolo[2,3-d]pyrimidines as janus kinase inhibitors |
| BRPI1012108B8 (pt) | 2009-05-22 | 2021-05-25 | Incyte Corp | composto 3-[4-(7h-pirrolo[2,3-d]pirimidin-4-il)-1h-pirazol-1-il]octa no- ou heptano-nitrila, sua composição, seus usos e processo para preparar um sal de ácido fosfórico |
| GEP20207129B (en) | 2009-06-17 | 2020-07-10 | Vertex Pharma | Inhibitors of influenza viruses replication |
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| EA202091303A3 (ru) | 2010-05-21 | 2021-05-31 | Инсайт Холдингс Корпорейшн | Композиция ингибитора jak для местного применения |
| ES2536415T3 (es) | 2010-11-19 | 2015-05-25 | Incyte Corporation | Pirrolopiridinas y pirrolopirimidinas sustituidas heterocíclicas como inhibidores de JAK |
| CA2818542A1 (en) | 2010-11-19 | 2012-05-24 | Incyte Corporation | Cyclobutyl substituted pyrrolopyridine and pyrrolopyrimidine derivatives as jak inhibitors |
| RU2013132681A (ru) | 2010-12-16 | 2015-01-27 | Вертекс Фармасьютикалз Инкорпорейтед | Ингибиторы репликации вирусов гриппа |
| US8691807B2 (en) | 2011-06-20 | 2014-04-08 | Incyte Corporation | Azetidinyl phenyl, pyridyl or pyrazinyl carboxamide derivatives as JAK inhibitors |
| UA118010C2 (uk) | 2011-08-01 | 2018-11-12 | Вертекс Фармасьютікалз Інкорпорейтед | Інгібітори реплікації вірусів грипу |
| TW201313721A (zh) | 2011-08-18 | 2013-04-01 | Incyte Corp | 作為ｊａｋ抑制劑之環己基氮雜環丁烷衍生物 |
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| TW201406761A (zh) | 2012-05-18 | 2014-02-16 | Incyte Corp | 做爲ｊａｋ抑制劑之哌啶基環丁基取代之吡咯并吡啶及吡咯并嘧啶衍生物 |
| JP6196678B2 (ja) | 2012-10-24 | 2017-09-13 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | Ｃ型肝炎ウイルス阻害剤 |
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| WO2014118388A1 (en) | 2013-02-04 | 2014-08-07 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for assaying jak2 activity in red blood cells and uses thereof |
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| ES2661012T3 (es) * | 2013-03-28 | 2018-03-27 | Takeda Pharmaceutical Company Limited | Compuesto heterocíclico |
| WO2014172639A1 (en) * | 2013-04-19 | 2014-10-23 | Ruga Corporation | Raf kinase inhibitors |
| CR20190156A (es) * | 2013-05-17 | 2019-05-16 | Incyte Corp | Derivados de bipirazol como inhibidores jak |
| MX376856B (es) | 2013-08-07 | 2025-03-07 | Incyte Holdings Corp | Formas de dosificacion de liberacion prolongada para un inhibidor de jak 1 (cinasa de janus 1). |
| HUE038820T2 (hu) | 2013-11-13 | 2018-11-28 | Vertex Pharma | Eljárás influenzavírusok replikációjának inhibitorai elõállítására |
| PT3068776T (pt) | 2013-11-13 | 2019-08-26 | Vertex Pharma | Inibidores da replicação de vírus da gripe |
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| US5728536A (en) | 1993-07-29 | 1998-03-17 | St. Jude Children's Research Hospital | Jak kinases and regulation of Cytokine signal transduction |
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-
2011
- 2011-04-11 KR KR1020127029826A patent/KR20130094710A/ko not_active Withdrawn
- 2011-04-11 US US13/640,099 patent/US8962596B2/en not_active Expired - Fee Related
- 2011-04-11 EP EP11715818.8A patent/EP2558468B1/en active Active
- 2011-04-11 WO PCT/US2011/031896 patent/WO2011130146A1/en not_active Ceased
- 2011-04-11 UA UAA201212901A patent/UA109131C2/ru unknown
- 2011-04-11 NZ NZ603446A patent/NZ603446A/en not_active IP Right Cessation
- 2011-04-11 MX MX2012011941A patent/MX2012011941A/es active IP Right Grant
- 2011-04-11 CN CN201180029128.5A patent/CN102985424B/zh not_active Expired - Fee Related
- 2011-04-11 PH PH1/2012/502046A patent/PH12012502046A1/en unknown
- 2011-04-11 SG SG2012076493A patent/SG184870A1/en unknown
- 2011-04-11 AU AU2011240808A patent/AU2011240808B2/en not_active Ceased
- 2011-04-11 CA CA2796388A patent/CA2796388A1/en not_active Abandoned
- 2011-04-11 JP JP2013504972A patent/JP2013523884A/ja not_active Ceased
- 2011-04-11 RU RU2012148246/04A patent/RU2012148246A/ru not_active Application Discontinuation
- 2011-04-13 UY UY0001033328A patent/UY33328A/es not_active Application Discontinuation
- 2011-04-13 AR ARP110101268A patent/AR081075A1/es not_active Application Discontinuation
- 2011-04-14 TW TW100113047A patent/TWI494314B/zh not_active IP Right Cessation
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2012
- 2012-10-12 CL CL2012002882A patent/CL2012002882A1/es unknown
- 2012-11-09 CR CR20120572A patent/CR20120572A/es unknown
- 2012-11-13 ZA ZA2012/08544A patent/ZA201208544B/en unknown
- 2012-11-13 CO CO12203751A patent/CO6630187A2/es active IP Right Grant
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2015
- 2015-06-26 JP JP2015128369A patent/JP2015205905A/ja active Pending
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