JP2012509940A5 - - Google Patents
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- Publication number
- JP2012509940A5 JP2012509940A5 JP2011538682A JP2011538682A JP2012509940A5 JP 2012509940 A5 JP2012509940 A5 JP 2012509940A5 JP 2011538682 A JP2011538682 A JP 2011538682A JP 2011538682 A JP2011538682 A JP 2011538682A JP 2012509940 A5 JP2012509940 A5 JP 2012509940A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrrol
- octahydrocyclopenta
- trifluoromethyl
- methyl
- phenyl
- 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.)
- Pending
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- -1 nitro, oxo, phenyl Chemical group 0.000 claims 201
- XPDWGBQVDMORPB-UHFFFAOYSA-N methyl trifluoride Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 claims 156
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 139
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 119
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 96
- 150000001408 amides Chemical class 0.000 claims 66
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 66
- 229910052739 hydrogen Inorganic materials 0.000 claims 61
- 239000001257 hydrogen Substances 0.000 claims 61
- 150000004657 carbamic acid derivatives Chemical compound 0.000 claims 55
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 40
- 125000000753 cycloalkyl group Chemical group 0.000 claims 29
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 28
- HBJGLYBWNNQMOW-LURJTMIESA-N (2S)-2-azaniumyl-2-methylpentanoate Chemical compound CCC[C@](C)(N)C(O)=O HBJGLYBWNNQMOW-LURJTMIESA-N 0.000 claims 24
- 125000003118 aryl group Chemical group 0.000 claims 22
- 125000001072 heteroaryl group Chemical group 0.000 claims 20
- 150000002431 hydrogen Chemical group 0.000 claims 20
- 150000001875 compounds Chemical class 0.000 claims 19
- 150000003839 salts Chemical class 0.000 claims 19
- 239000011780 sodium chloride Substances 0.000 claims 19
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 15
- 125000005418 aryl aryl group Chemical group 0.000 claims 14
- 125000004432 carbon atoms Chemical group C* 0.000 claims 12
- 125000000623 heterocyclic group Chemical group 0.000 claims 11
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 10
- DLFVBJFMPXGRIB-UHFFFAOYSA-N acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 9
- 229910052736 halogen Inorganic materials 0.000 claims 9
- 150000002367 halogens Chemical class 0.000 claims 9
- 125000005842 heteroatoms Chemical group 0.000 claims 8
- 150000003869 acetamides Chemical compound 0.000 claims 7
- IPWFJLQDVFKJDU-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O IPWFJLQDVFKJDU-UHFFFAOYSA-N 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- 229910052717 sulfur Inorganic materials 0.000 claims 7
- 125000004105 2-pyridyl group Chemical compound N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 6
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000003277 amino group Chemical compound 0.000 claims 6
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 6
- 208000002193 Pain Diseases 0.000 claims 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 5
- 125000004122 cyclic group Chemical group 0.000 claims 5
- 125000002950 monocyclic group Chemical group 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 4
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims 4
- NPDWHDXPQPMHJR-UHFFFAOYSA-M CCCC(C)NC([O-])=O Chemical compound CCCC(C)NC([O-])=O NPDWHDXPQPMHJR-UHFFFAOYSA-M 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000001449 isopropyl group Chemical compound [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 4
- 125000003548 sec-pentyl group Chemical compound [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 4
- QCIGLPLDNRDLQQ-UHFFFAOYSA-M N-butan-2-ylcarbamate Chemical compound CCC(C)NC([O-])=O QCIGLPLDNRDLQQ-UHFFFAOYSA-M 0.000 claims 3
- 125000002619 bicyclic group Chemical group 0.000 claims 3
- 125000004367 cycloalkylaryl group Chemical group 0.000 claims 3
- XNEFVTBPCXGIRX-UHFFFAOYSA-M methanesulfinate Chemical compound CS([O-])=O XNEFVTBPCXGIRX-UHFFFAOYSA-M 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- HZMVPSHLMIQQNX-UHFFFAOYSA-N pentan-2-yl carbamate Chemical compound CCCC(C)OC(N)=O HZMVPSHLMIQQNX-UHFFFAOYSA-N 0.000 claims 3
- 125000005931 tert-butyloxycarbonyl group Chemical compound [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- WAUGGYPDCQZJKK-UHFFFAOYSA-N 1H-pyrrol-3-amine Chemical compound NC=1C=CNC=1 WAUGGYPDCQZJKK-UHFFFAOYSA-N 0.000 claims 2
- 125000002981 3-(trifluoromethyl)benzoyl group Chemical compound FC(C=1C=C(C(=O)*)C=CC1)(F)F 0.000 claims 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 2
- 206010004938 Bipolar disease Diseases 0.000 claims 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N Ethyl radical Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims 2
- 206010027599 Migraine Diseases 0.000 claims 2
- 208000008085 Migraine Disorders Diseases 0.000 claims 2
- QLNJFJADRCOGBJ-UHFFFAOYSA-N Propanamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 2
- 125000004429 atoms Chemical group 0.000 claims 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 125000004051 hexyl group Chemical compound [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- YNTOKMNHRPSGFU-UHFFFAOYSA-N n-Propyl carbamate Chemical compound CCCOC(N)=O YNTOKMNHRPSGFU-UHFFFAOYSA-N 0.000 claims 2
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 125000004528 pyrimidin-5-yl group Chemical compound N1=CN=CC(=C1)* 0.000 claims 2
- 125000000169 tricyclic heterocycle group Chemical group 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- AFYSEMLDHWBGBG-LUKWVAJMSA-N (2R)-N-[(3aR,4S,6aS)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-2-phenylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)[C@H](CC)C=2C=CC=CC=2)N1CC1=CC=CC=C1 AFYSEMLDHWBGBG-LUKWVAJMSA-N 0.000 claims 1
- ZIIGNHNCZKJHGP-GFRNBQLOSA-N (2R)-N-[(3aR,4S,6aS)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-2-phenylpropanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)[C@H](C)C=2C=CC=CC=2)N1CC1=CC=CC=C1 ZIIGNHNCZKJHGP-GFRNBQLOSA-N 0.000 claims 1
- ZHCVAQPWDAYWNI-OLKYXYMISA-N (2R)-N-[(3aS,4R,6aR)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-3,3-dimethyl-2-phenylbutanamide Chemical compound C([C@@H]1CC[C@H]([C@@H]1C1)NC(=O)[C@H](C(C)(C)C)C=2C=CC=CC=2)N1CC1=CC=CC=C1 ZHCVAQPWDAYWNI-OLKYXYMISA-N 0.000 claims 1
- KIHNPRLURCOJPM-MNAPGUCWSA-N (2S)-N-[(3aR,4S,6aS)-2-(4-fluorophenyl)sulfonyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-2-(2,2-dimethylpropylamino)-4-methylpentanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)[C@@H](NCC(C)(C)C)CC(C)C)N1S(=O)(=O)C1=CC=C(F)C=C1 KIHNPRLURCOJPM-MNAPGUCWSA-N 0.000 claims 1
- XGHGKVOKFBNHFC-QCSYZSNVSA-N (2S)-N-[(3aR,4S,6aS)-2-[3-(trifluoromethyl)phenyl]sulfonyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]piperidine-2-carboxamide Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)N2C[C@@H]3[C@@H](NC(=O)[C@H]4NCCCC4)CC[C@@H]3C2)=C1 XGHGKVOKFBNHFC-QCSYZSNVSA-N 0.000 claims 1
- VFMZAEZBXACMRF-QKDIEKDRSA-N (2S)-N-[(3aR,4S,6aS)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-2-[4-(2-methylpropyl)phenyl]propanamide Chemical compound C1=CC(CC(C)C)=CC=C1[C@H](C)C(=O)N[C@@H]1[C@H]2CN(CC=3C=CC=CC=3)C[C@H]2CC1 VFMZAEZBXACMRF-QKDIEKDRSA-N 0.000 claims 1
- AFYSEMLDHWBGBG-LDVJMBRRSA-N (2S)-N-[(3aR,4S,6aS)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-2-phenylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)[C@@H](CC)C=2C=CC=CC=2)N1CC1=CC=CC=C1 AFYSEMLDHWBGBG-LDVJMBRRSA-N 0.000 claims 1
- ZIIGNHNCZKJHGP-XGARDCMYSA-N (2S)-N-[(3aR,4S,6aS)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-2-phenylpropanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)[C@@H](C)C=2C=CC=CC=2)N1CC1=CC=CC=C1 ZIIGNHNCZKJHGP-XGARDCMYSA-N 0.000 claims 1
- XBFYNDXHJCGGBE-FYQPLNBISA-N (2S)-N-[(3aR,4S,6aS)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-4-methyl-2-(methylamino)pentanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)[C@H](CC(C)C)NC)N1CC1=CC=CC=C1 XBFYNDXHJCGGBE-FYQPLNBISA-N 0.000 claims 1
- JIJXKKFQLDKTJP-LIRZEXBASA-N (2S)-N-[(3aS,4R,6aR)-2-(4-fluorophenyl)sulfonyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]piperidine-2-carboxamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)N1C[C@H]2[C@H](NC(=O)[C@H]3NCCCC3)CC[C@H]2C1 JIJXKKFQLDKTJP-LIRZEXBASA-N 0.000 claims 1
- WQZWOLQTLQNVGD-OTGYPNLISA-N (2S)-N-[(3aS,4R,6aR)-2-[(1S)-1-phenylethyl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-2-phenylbutanamide Chemical compound C1([C@H](C)N2C[C@@H]3CC[C@H]([C@@H]3C2)NC(=O)[C@@H](CC)C=2C=CC=CC=2)=CC=CC=C1 WQZWOLQTLQNVGD-OTGYPNLISA-N 0.000 claims 1
- PJQNPTHRIJPDSO-AITUJVMLSA-N (2S)-N-[(3aS,4R,6aR)-2-[(4-fluorophenyl)methyl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]piperidine-2-carboxamide Chemical compound C1=CC(F)=CC=C1CN1C[C@H]2[C@H](NC(=O)[C@H]3NCCCC3)CC[C@H]2C1 PJQNPTHRIJPDSO-AITUJVMLSA-N 0.000 claims 1
- XGHGKVOKFBNHFC-LIRZEXBASA-N (2S)-N-[(3aS,4R,6aR)-2-[3-(trifluoromethyl)phenyl]sulfonyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]piperidine-2-carboxamide Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)N2C[C@H]3[C@H](NC(=O)[C@H]4NCCCC4)CC[C@H]3C2)=C1 XGHGKVOKFBNHFC-LIRZEXBASA-N 0.000 claims 1
- XHAOOIHWQCRONK-LIRZEXBASA-N (2S)-N-[(3aS,4R,6aR)-2-[4-(trifluoromethyl)phenyl]sulfonyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]piperidine-2-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1S(=O)(=O)N1C[C@H]2[C@H](NC(=O)[C@H]3NCCCC3)CC[C@H]2C1 XHAOOIHWQCRONK-LIRZEXBASA-N 0.000 claims 1
- XBKSTLUJFXKPCT-AITUJVMLSA-N (2S)-N-[(3aS,4R,6aR)-2-[[4-(trifluoromethyl)phenyl]methyl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]piperidine-2-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1CN1C[C@H]2[C@H](NC(=O)[C@H]3NCCCC3)CC[C@H]2C1 XBKSTLUJFXKPCT-AITUJVMLSA-N 0.000 claims 1
- AXLLRPUTJGXBNO-AFXVXQJMSA-N (2S)-N-[(3aS,4R,6aR)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-2-(2,2-dimethylpropylamino)-4-methylpentanamide Chemical compound C([C@@H]1CC[C@H]([C@@H]1C1)NC(=O)[C@@H](NCC(C)(C)C)CC(C)C)N1CC1=CC=CC=C1 AXLLRPUTJGXBNO-AFXVXQJMSA-N 0.000 claims 1
- AFYSEMLDHWBGBG-MYDTUXCISA-N (2S)-N-[(3aS,4R,6aR)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-2-phenylbutanamide Chemical compound C([C@@H]1CC[C@H]([C@@H]1C1)NC(=O)[C@@H](CC)C=2C=CC=CC=2)N1CC1=CC=CC=C1 AFYSEMLDHWBGBG-MYDTUXCISA-N 0.000 claims 1
- ZIIGNHNCZKJHGP-GUGJDKNPSA-N (2S)-N-[(3aS,4R,6aR)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-2-phenylpropanamide Chemical compound C([C@@H]1CC[C@H]([C@@H]1C1)NC(=O)[C@@H](C)C=2C=CC=CC=2)N1CC1=CC=CC=C1 ZIIGNHNCZKJHGP-GUGJDKNPSA-N 0.000 claims 1
- ZHCVAQPWDAYWNI-KEZOAJOQSA-N (2S)-N-[(3aS,4R,6aR)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-3,3-dimethyl-2-phenylbutanamide Chemical compound C([C@@H]1CC[C@H]([C@@H]1C1)NC(=O)[C@@H](C(C)(C)C)C=2C=CC=CC=2)N1CC1=CC=CC=C1 ZHCVAQPWDAYWNI-KEZOAJOQSA-N 0.000 claims 1
- NUBHGCWUZZYQCT-AFXVXQJMSA-N (2S)-N-[(3aS,4R,6aR)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-4-methyl-2-morpholin-4-ylpentanamide Chemical compound N1([C@@H](CC(C)C)C(=O)N[C@H]2[C@@H]3CN(CC=4C=CC=CC=4)C[C@@H]3CC2)CCOCC1 NUBHGCWUZZYQCT-AFXVXQJMSA-N 0.000 claims 1
- DFHVCZMXZUUYEF-KEZOAJOQSA-N (2S)-N-[(3aS,4R,6aR)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-4-methyl-2-piperidin-1-ylpentanamide Chemical compound N1([C@@H](CC(C)C)C(=O)N[C@H]2[C@@H]3CN(CC=4C=CC=CC=4)C[C@@H]3CC2)CCCCC1 DFHVCZMXZUUYEF-KEZOAJOQSA-N 0.000 claims 1
- MMAPUUNPFVWZNT-AFXVXQJMSA-N (2S)-N-[(3aS,4R,6aR)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-4-methyl-2-pyrrolidin-1-ylpentanamide Chemical compound N1([C@@H](CC(C)C)C(=O)N[C@H]2[C@@H]3CN(CC=4C=CC=CC=4)C[C@@H]3CC2)CCCC1 MMAPUUNPFVWZNT-AFXVXQJMSA-N 0.000 claims 1
- FDNJHAFULMBTQR-MANSERQUSA-N (2S)-N-[(3aS,4R,6aR)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]piperidine-2-carboxamide Chemical compound C([C@@H]1CC[C@H]([C@@H]1C1)NC(=O)[C@H]2NCCCC2)N1CC1=CC=CC=C1 FDNJHAFULMBTQR-MANSERQUSA-N 0.000 claims 1
- QOBBCGKBMUMPEY-AITUJVMLSA-N (2S)-N-[(3aS,4R,6aR)-2-cyclopropylsulfonyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-4-methyl-2-pyrrolidin-1-ylpentanamide Chemical compound N1([C@@H](CC(C)C)C(=O)N[C@H]2[C@@H]3CN(C[C@@H]3CC2)S(=O)(=O)C2CC2)CCCC1 QOBBCGKBMUMPEY-AITUJVMLSA-N 0.000 claims 1
- UEDWLWBUBRWATL-HZMVEIRTSA-N (2S)-N-[(3aS,4R,6aR)-2-methylsulfonyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-4-methyl-2-pyrrolidin-1-ylpentanamide Chemical compound N1([C@@H](CC(C)C)C(=O)N[C@H]2[C@@H]3CN(C[C@@H]3CC2)S(C)(=O)=O)CCCC1 UEDWLWBUBRWATL-HZMVEIRTSA-N 0.000 claims 1
- DGNINGBAZJPLSW-INWMFGNUSA-N (3aR,4S,6aS)-2-[2-chloro-4-(trifluoromethyl)phenyl]sulfonyl-N,N-diethyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-amine Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)N(CC)CC)N1S(=O)(=O)C1=CC=C(C(F)(F)F)C=C1Cl DGNINGBAZJPLSW-INWMFGNUSA-N 0.000 claims 1
- XKAWHGWXUGNVQR-WPGHFRTFSA-N (3aR,4S,6aS)-2-[2-chloro-4-(trifluoromethyl)phenyl]sulfonyl-N-[5-(trifluoromethyl)pyridin-2-yl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-amine Chemical compound N1=CC(C(F)(F)F)=CC=C1N[C@@H]1[C@H]2CN(S(=O)(=O)C=3C(=CC(=CC=3)C(F)(F)F)Cl)C[C@H]2CC1 XKAWHGWXUGNVQR-WPGHFRTFSA-N 0.000 claims 1
- RXWBIZNXTMGFAV-OSMZGAPFSA-N (3aR,4S,6aS)-2-[2-chloro-4-(trifluoromethyl)phenyl]sulfonyl-N-ethyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-amine Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NCC)N1S(=O)(=O)C1=CC=C(C(F)(F)F)C=C1Cl RXWBIZNXTMGFAV-OSMZGAPFSA-N 0.000 claims 1
- BPRGUKOJPVNZHW-ZLDLUXBVSA-N (3aR,4S,6aS)-2-[2-chloro-4-(trifluoromethyl)phenyl]sulfonyl-N-propan-2-yl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-amine Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(C)C)N1S(=O)(=O)C1=CC=C(C(F)(F)F)C=C1Cl BPRGUKOJPVNZHW-ZLDLUXBVSA-N 0.000 claims 1
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- BFMZOFRSTNVLKU-UZGMISGMSA-N N-[(3aR,4S,6aS)-2-[3-(3-fluorophenyl)propyl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-3-methyl-2-phenylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C(C)C)C=2C=CC=CC=2)N1CCCC1=CC=CC(F)=C1 BFMZOFRSTNVLKU-UZGMISGMSA-N 0.000 claims 1
- DEWZDZQKZHTKMB-RAMLRSSZSA-N N-[(3aR,4S,6aS)-2-[3-(3-methylphenyl)propyl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-3-methyl-2-phenylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C(C)C)C=2C=CC=CC=2)N1CCCC1=CC=CC(C)=C1 DEWZDZQKZHTKMB-RAMLRSSZSA-N 0.000 claims 1
- RNDDOHQGBFHRRD-PLFRKVQXSA-N N-[(3aR,4S,6aS)-2-[3-(4-tert-butylphenyl)propyl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-3-methyl-2-phenylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C(C)C)C=2C=CC=CC=2)N1CCCC1=CC=C(C(C)(C)C)C=C1 RNDDOHQGBFHRRD-PLFRKVQXSA-N 0.000 claims 1
- NDMXQOUDOHEXMV-UZGMISGMSA-N N-[(3aR,4S,6aS)-2-[3-[3-(trifluoromethyl)phenyl]propyl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-3-methyl-2-phenylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C(C)C)C=2C=CC=CC=2)N1CCCC1=CC=CC(C(F)(F)F)=C1 NDMXQOUDOHEXMV-UZGMISGMSA-N 0.000 claims 1
- VTWSFYYTEQRDKR-UZGMISGMSA-N N-[(3aR,4S,6aS)-2-[3-[4-(trifluoromethyl)phenyl]propyl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-3-methyl-2-phenylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C(C)C)C=2C=CC=CC=2)N1CCCC1=CC=C(C(F)(F)F)C=C1 VTWSFYYTEQRDKR-UZGMISGMSA-N 0.000 claims 1
- LIDPUHPUOYOHKJ-HOMPBRHSSA-N N-[(3aR,4S,6aS)-2-[4,4-bis(4-fluorophenyl)butyl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-3-methyl-2-phenylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C(C)C)C=2C=CC=CC=2)N1CCCC(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 LIDPUHPUOYOHKJ-HOMPBRHSSA-N 0.000 claims 1
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- BRFLFYAITKCSIZ-GYGZHRCXSA-N N-[(3aR,4S,6aS)-2-[6,6-bis(4-fluorophenyl)hexyl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-3-methyl-2-phenylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C(C)C)C=2C=CC=CC=2)N1CCCCCC(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 BRFLFYAITKCSIZ-GYGZHRCXSA-N 0.000 claims 1
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- WRHXIEPCASAPCY-ZRSRXCJOSA-N N-[(3aR,4S,6aS)-2-[[2-(trifluoromethyl)phenyl]methyl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-3-methyl-2-phenylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C(C)C)C=2C=CC=CC=2)N1CC1=CC=CC=C1C(F)(F)F WRHXIEPCASAPCY-ZRSRXCJOSA-N 0.000 claims 1
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- HDNWDHPPQXTLRY-JDMZLTFJSA-N N-[(3aR,4S,6aS)-2-[[4-(trifluoromethyl)phenyl]methyl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-3-methyl-2-phenylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C(C)C)C=2C=CC=CC=2)N1CC1=CC=C(C(F)(F)F)C=C1 HDNWDHPPQXTLRY-JDMZLTFJSA-N 0.000 claims 1
- FBUNVEFOYSAPBM-LSSMUYGWSA-N N-[(3aR,4S,6aS)-2-[[4-fluoro-3-(trifluoromethyl)phenyl]methyl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-3-methyl-2-phenylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C(C)C)C=2C=CC=CC=2)N1CC1=CC=C(F)C(C(F)(F)F)=C1 FBUNVEFOYSAPBM-LSSMUYGWSA-N 0.000 claims 1
- NATSUVQXKCVDKZ-ZFSMBLLKSA-N N-[(3aR,4S,6aS)-2-benzoyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-3-methyl-2-phenylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C(C)C)C=2C=CC=CC=2)N1C(=O)C1=CC=CC=C1 NATSUVQXKCVDKZ-ZFSMBLLKSA-N 0.000 claims 1
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- IQEVAHZYBSUYPP-RZFJZAQRSA-N N-[(3aR,4S,6aS)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-2,2-bis(4-fluorophenyl)acetamide Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)C(=O)N[C@@H]1[C@H]2CN(CC=3C=CC=CC=3)C[C@H]2CC1 IQEVAHZYBSUYPP-RZFJZAQRSA-N 0.000 claims 1
- USIBBSAAJMNUPN-ZNZIZOMTSA-N N-[(3aR,4S,6aS)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-2,2-dicyclohexylacetamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C2CCCCC2)C2CCCCC2)N1CC1=CC=CC=C1 USIBBSAAJMNUPN-ZNZIZOMTSA-N 0.000 claims 1
- KQQJEVURYCVLGV-LBSFNXSNSA-N N-[(3aR,4S,6aS)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-2,3-diphenylpropanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(CC=2C=CC=CC=2)C=2C=CC=CC=2)N1CC1=CC=CC=C1 KQQJEVURYCVLGV-LBSFNXSNSA-N 0.000 claims 1
- MMRDVXCWKZHBDM-JDMZLTFJSA-N N-[(3aR,4S,6aS)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-2-(4-chlorophenyl)-3-methylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C(C)C)C=2C=CC(Cl)=CC=2)N1CC1=CC=CC=C1 MMRDVXCWKZHBDM-JDMZLTFJSA-N 0.000 claims 1
- STTSBVHXFVXHRR-JDMZLTFJSA-N N-[(3aR,4S,6aS)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-2-(4-hydroxyphenyl)-3-methylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C(C)C)C=2C=CC(O)=CC=2)N1CC1=CC=CC=C1 STTSBVHXFVXHRR-JDMZLTFJSA-N 0.000 claims 1
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- JEXAZUMKXNHAFK-XXRNLSRLSA-N N-[(3aR,4S,6aS)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-2-cyclobutyl-2-phenylacetamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C2CCC2)C=2C=CC=CC=2)N1CC1=CC=CC=C1 JEXAZUMKXNHAFK-XXRNLSRLSA-N 0.000 claims 1
- BDECLCVAQQPYIA-VHNWMKGBSA-N N-[(3aR,4S,6aS)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-2-cyclopentyl-2-phenylacetamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C2CCCC2)C=2C=CC=CC=2)N1CC1=CC=CC=C1 BDECLCVAQQPYIA-VHNWMKGBSA-N 0.000 claims 1
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- ZOWLHDAHUAMRTQ-HJNYFJLDSA-N N-[(3aR,4S,6aS)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-2-methyl-2-phenylpropanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C)(C)C=2C=CC=CC=2)N1CC1=CC=CC=C1 ZOWLHDAHUAMRTQ-HJNYFJLDSA-N 0.000 claims 1
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- ZHCVAQPWDAYWNI-XDXUOVRZSA-N N-[(3aR,4S,6aS)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-3,3-dimethyl-2-phenylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C(C)(C)C)C=2C=CC=CC=2)N1CC1=CC=CC=C1 ZHCVAQPWDAYWNI-XDXUOVRZSA-N 0.000 claims 1
- AEHLVQDFIMVPSJ-VHNWMKGBSA-N N-[(3aR,4S,6aS)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-3-ethyl-2-phenylpentanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C(CC)CC)C=2C=CC=CC=2)N1CC1=CC=CC=C1 AEHLVQDFIMVPSJ-VHNWMKGBSA-N 0.000 claims 1
- HEVYJRZHYSRHDM-XDXUOVRZSA-N N-[(3aR,4S,6aS)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-3-methyl-2-phenylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C(C)C)C=2C=CC=CC=2)N1CC1=CC=CC=C1 HEVYJRZHYSRHDM-XDXUOVRZSA-N 0.000 claims 1
- PDFATPKTQIBOSI-AABGKKOBSA-N N-[(3aR,4S,6aS)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-3-methyl-2-propan-2-ylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)C(C(C)C)C(C)C)N1CC1=CC=CC=C1 PDFATPKTQIBOSI-AABGKKOBSA-N 0.000 claims 1
- IHQZJMDOKJOKIE-SQNIBIBYSA-N N-[(3aR,4S,6aS)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-3-methylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)NC(=O)CC(C)C)N1CC1=CC=CC=C1 IHQZJMDOKJOKIE-SQNIBIBYSA-N 0.000 claims 1
- CNBIUZXLXDADDC-XXRNLSRLSA-N N-[(3aR,4S,6aS)-2-benzyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-N,3-dimethyl-2-phenylbutanamide Chemical compound C([C@H]1CC[C@@H]([C@H]1C1)N(C)C(=O)C(C(C)C)C=2C=CC=CC=2)N1CC1=CC=CC=C1 CNBIUZXLXDADDC-XXRNLSRLSA-N 0.000 claims 1
- BGZOADFLQOFKNC-KKSQLVLISA-N N-[(3aR,4S,6aS)-2-methyl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-3-methyl-2-phenylbutanamide Chemical compound N([C@@H]1[C@H]2CN(C)C[C@H]2CC1)C(=O)C(C(C)C)C1=CC=CC=C1 BGZOADFLQOFKNC-KKSQLVLISA-N 0.000 claims 1
- LCHOSRIKTHYCQA-IPMKNSEASA-N N-[(3aS,4R,6aR)-1,2,3,3a,4,5,6,6a-octahydrocyclopenta[c]pyrrol-4-yl]-2,2-dicyclohexylacetamide Chemical compound N([C@H]1[C@@H]2CNC[C@@H]2CC1)C(=O)C(C1CCCCC1)C1CCCCC1 LCHOSRIKTHYCQA-IPMKNSEASA-N 0.000 claims 1
- WNPKHVYUJWDHTA-HEAIWMBWSA-N N-[(3aS,4R,6aR)-2-(3,3-diphenylpropyl)-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-2,2-dicyclohexylacetamide Chemical compound C([C@@H]1CC[C@H]([C@@H]1C1)NC(=O)C(C2CCCCC2)C2CCCCC2)N1CCC(C=1C=CC=CC=1)C1=CC=CC=C1 WNPKHVYUJWDHTA-HEAIWMBWSA-N 0.000 claims 1
- NAHLNYDVBZOUFA-BKKFENPESA-N N-[(3aS,4R,6aR)-2-[(2R)-2-(dimethylamino)-4-methylpentanoyl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-2,2-dicyclohexylacetamide Chemical compound N([C@@H]1CC[C@H]2CN(C[C@H]21)C(=O)[C@H](N(C)C)CC(C)C)C(=O)C(C1CCCCC1)C1CCCCC1 NAHLNYDVBZOUFA-BKKFENPESA-N 0.000 claims 1
- SIYCCBZZNCPXKJ-AQEWBBHDSA-N N-[(3aS,4R,6aR)-2-[3,3-bis(4-fluorophenyl)propyl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-2,2-dicyclohexylacetamide Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCN1C[C@H]2[C@H](NC(=O)C(C3CCCCC3)C3CCCCC3)CC[C@H]2C1 SIYCCBZZNCPXKJ-AQEWBBHDSA-N 0.000 claims 1
- FLWIQOZBJZNRSS-KGJXQKDRSA-N N-[(3aS,4R,6aR)-2-[4,4-bis(4-fluorophenyl)butyl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-4-yl]-2,2-dicyclohexylacetamide Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCN1C[C@H]2[C@H](NC(=O)C(C3CCCCC3)C3CCCCC3)CC[C@H]2C1 FLWIQOZBJZNRSS-KGJXQKDRSA-N 0.000 claims 1
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| CA2742350A1 (en) | 2008-11-26 | 2010-06-03 | Abbott Laboratories | Novel substituted octahydrocyclopenta(c)pyrrol-4-amines as calcium channel blockers |
| US8691865B2 (en) | 2008-11-26 | 2014-04-08 | Abbvie Inc. | Substituted octahydrocyclopenta[C]pyrrol-4-amines as calcium channel blockers |
| US8211933B2 (en) | 2008-12-12 | 2012-07-03 | Vanderbilt University | 3.3.0 bicyclic GlyT1 inhibitors and methods of making and using same |
| WO2011115813A1 (en) * | 2010-03-18 | 2011-09-22 | Abbott Laboratories | Lactam acetamides as calcium channel blockers |
| US8796470B2 (en) | 2010-05-25 | 2014-08-05 | Abbvie Inc. | Substituted octahydrocyclopenta[c]pyrroles as calcium channel modulators |
| FR2976285B1 (fr) * | 2011-06-08 | 2013-05-24 | Servier Lab | Procede de synthese et forme cristalline du chlorhydrate de 4-{3-[cis-hexahydrocypenta[c]pyrrol-2(1h)-yl]propoxy}benzamide ainsi que les compositions pharmaceutiques qui la contiennent |
| US8669255B2 (en) | 2011-09-29 | 2014-03-11 | Abbvie Inc. | Substituted octahydropyrrolo[1,2-a]pyrazines as calcium channel blockers |
| TW201321384A (zh) | 2011-09-29 | 2013-06-01 | Abbvie Inc | 作為鈣通道阻斷劑之經取代之八氫吡咯并［１，２－ａ］吡□磺醯胺 |
| WO2014093337A1 (en) | 2012-12-12 | 2014-06-19 | Abbvie, Inc. | Diazepine derivatives useful as calcium channel blockers in the treatment of pain |
| CN107849009B (zh) * | 2015-10-13 | 2021-03-02 | 四川海思科制药有限公司 | 一种八氢环戊二烯并[c]吡咯衍生物及其制备方法和在医药上的用途 |
| CN111201223B (zh) * | 2017-09-11 | 2024-07-09 | 克鲁松制药公司 | SHP2的八氢环戊二烯并[c]吡咯别构抑制剂 |
| EA202092086A1 (ru) | 2018-03-05 | 2021-02-09 | Аркус Байосайенсиз, Инк. | Ингибиторы аргиназы |
| KR20230166084A (ko) | 2021-04-01 | 2023-12-06 | 오노 야꾸힝 고교 가부시키가이샤 | Abhd6 안타고니스트 |
| KR20240046089A (ko) | 2022-09-30 | 2024-04-08 | 오노 야꾸힝 고교 가부시키가이샤 | Abhd6 길항제를 함유하는 약학 조성물 |
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| JPH0278659A (ja) * | 1988-09-12 | 1990-03-19 | Shionogi & Co Ltd | アザビシクロアルカン類化合物 |
| ATE269848T1 (de) | 1999-04-07 | 2004-07-15 | Univ Virginia | Calciumkanalblocker als antikrebsmittel |
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| US7223754B2 (en) * | 2003-03-10 | 2007-05-29 | Dynogen Pharmaceuticals, Inc. | Thiazolidinone, oxazolidinone, and imidazolone derivatives for treating lower urinary tract and related disorders |
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| US7230022B2 (en) * | 2004-02-19 | 2007-06-12 | Bristol-Myers Squibb Company | Substituted fused bicyclic amines as modulators of chemokine receptor activity |
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| DE102004039789A1 (de) * | 2004-08-16 | 2006-03-02 | Sanofi-Aventis Deutschland Gmbh | Arylsubstituierte polycyclische Amine, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| CN101163482A (zh) * | 2005-04-19 | 2008-04-16 | 默克公司 | N－烷基－氮杂环烷基nmda/nr2b拮抗剂 |
| EP2350002A1 (en) * | 2008-10-02 | 2011-08-03 | Abbott Laboratories | Novel compounds as calcium channel blockers |
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| US8211933B2 (en) | 2008-12-12 | 2012-07-03 | Vanderbilt University | 3.3.0 bicyclic GlyT1 inhibitors and methods of making and using same |
-
2009
- 2009-11-25 CA CA2742350A patent/CA2742350A1/en not_active Abandoned
- 2009-11-25 BR BRPI0921184A patent/BRPI0921184A2/pt not_active IP Right Cessation
- 2009-11-25 TW TW098140141A patent/TW201028378A/zh unknown
- 2009-11-25 US US12/625,754 patent/US8129417B2/en not_active Expired - Fee Related
- 2009-11-25 PE PE2011001093A patent/PE20110833A1/es not_active Application Discontinuation
- 2009-11-25 EP EP09764953A patent/EP2367790A2/en not_active Withdrawn
- 2009-11-25 WO PCT/US2009/065847 patent/WO2010062927A2/en active Application Filing
- 2009-11-25 MX MX2011005537A patent/MX2011005537A/es unknown
- 2009-11-25 PA PA20098850301A patent/PA8850301A1/es unknown
- 2009-11-25 CN CN2009801553748A patent/CN102292319A/zh active Pending
- 2009-11-25 NZ NZ592507A patent/NZ592507A/xx not_active IP Right Cessation
- 2009-11-25 UY UY0001032261A patent/UY32261A/es not_active Application Discontinuation
- 2009-11-25 AR ARP090104557A patent/AR074226A1/es not_active Application Discontinuation
- 2009-11-25 RU RU2011126215/04A patent/RU2011126215A/ru not_active Application Discontinuation
- 2009-11-25 AU AU2009319796A patent/AU2009319796A1/en not_active Abandoned
- 2009-11-25 JP JP2011538682A patent/JP2012509940A/ja active Pending
- 2009-11-25 KR KR1020117014731A patent/KR20110091784A/ko not_active Application Discontinuation
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2011
- 2011-04-26 IL IL212484A patent/IL212484A0/en unknown
- 2011-05-13 ZA ZA2011/03538A patent/ZA201103538B/en unknown
- 2011-05-19 CL CL2011001176A patent/CL2011001176A1/es unknown
- 2011-05-27 CO CO11065858A patent/CO6382118A2/es not_active Application Discontinuation
- 2011-06-06 CR CR20110304A patent/CR20110304A/es not_active Application Discontinuation
- 2011-06-24 EC EC2011011160A patent/ECSP11011160A/es unknown
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