KR20100134680A - 스테아로일-coa 불포화효소의 저해물질로서 신규한 피페리딘 유도체 - Google Patents
스테아로일-coa 불포화효소의 저해물질로서 신규한 피페리딘 유도체 Download PDFInfo
- Publication number
- KR20100134680A KR20100134680A KR1020107023415A KR20107023415A KR20100134680A KR 20100134680 A KR20100134680 A KR 20100134680A KR 1020107023415 A KR1020107023415 A KR 1020107023415A KR 20107023415 A KR20107023415 A KR 20107023415A KR 20100134680 A KR20100134680 A KR 20100134680A
- Authority
- KR
- South Korea
- Prior art keywords
- oxo
- ethyl
- piperidin
- carboxylic acid
- 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.)
- Ceased
Links
- 108010087894 Fatty acid desaturases Proteins 0.000 title claims abstract description 9
- 239000003112 inhibitor Substances 0.000 title claims abstract description 7
- 102000016553 Stearoyl-CoA Desaturase Human genes 0.000 title claims abstract 4
- 150000003053 piperidines Chemical class 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 175
- 238000000034 method Methods 0.000 claims abstract description 43
- -1 cyano, nitro, amino Chemical group 0.000 claims description 258
- 125000000217 alkyl group Chemical group 0.000 claims description 93
- 125000003118 aryl group Chemical group 0.000 claims description 90
- 125000001072 heteroaryl group Chemical group 0.000 claims description 79
- 150000003839 salts Chemical class 0.000 claims description 79
- 229910052739 hydrogen Inorganic materials 0.000 claims description 67
- 239000001257 hydrogen Substances 0.000 claims description 67
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 65
- 239000012453 solvate Substances 0.000 claims description 57
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 49
- 201000010099 disease Diseases 0.000 claims description 43
- 229910052736 halogen Inorganic materials 0.000 claims description 42
- 150000002367 halogens Chemical class 0.000 claims description 42
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 36
- 125000000623 heterocyclic group Chemical group 0.000 claims description 32
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000003282 alkyl amino group Chemical group 0.000 claims description 19
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 19
- 150000001721 carbon Chemical group 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 150000002431 hydrogen Chemical class 0.000 claims description 18
- 125000000304 alkynyl group Chemical group 0.000 claims description 17
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 208000008589 Obesity Diseases 0.000 claims description 15
- 125000003435 aroyl group Chemical group 0.000 claims description 15
- 125000001769 aryl amino group Chemical group 0.000 claims description 15
- 235000020824 obesity Nutrition 0.000 claims description 15
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 14
- 125000002252 acyl group Chemical group 0.000 claims description 14
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 14
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 14
- 125000003368 amide group Chemical group 0.000 claims description 14
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 14
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 14
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 14
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 14
- 125000005110 aryl thio group Chemical group 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 14
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 14
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 14
- 125000004986 diarylamino group Chemical group 0.000 claims description 14
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 14
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 14
- 125000005226 heteroaryloxycarbonyl group Chemical group 0.000 claims description 14
- 125000005150 heteroarylsulfinyl group Chemical group 0.000 claims description 14
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 14
- 150000004677 hydrates Chemical class 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- GFQYKYPGSBTSII-HHHXNRCGSA-N 4-[[(2r)-2-methyl-6-nitro-3h-imidazo[2,1-b][1,3]oxazol-2-yl]methoxy]-n-[2-oxo-2-[4-[4-(trifluoromethoxy)phenoxy]piperidin-1-yl]ethyl]benzamide Chemical compound C([C@]1(C)OC2=NC(=CN2C1)[N+]([O-])=O)OC(C=C1)=CC=C1C(=O)NCC(=O)N(CC1)CCC1OC1=CC=C(OC(F)(F)F)C=C1 GFQYKYPGSBTSII-HHHXNRCGSA-N 0.000 claims description 8
- AAJYKZWEWUTPKH-UHFFFAOYSA-N 5-anilino-n-[2-[4-(2-chloroanilino)piperidin-1-yl]-2-oxoethyl]pyridine-2-carboxamide Chemical compound ClC1=CC=CC=C1NC1CCN(C(=O)CNC(=O)C=2N=CC(NC=3C=CC=CC=3)=CC=2)CC1 AAJYKZWEWUTPKH-UHFFFAOYSA-N 0.000 claims description 6
- VLZSMKGNKCKWGB-UHFFFAOYSA-N 1-(2-cyanophenyl)-n-[2-oxo-2-[4-[3-(trifluoromethyl)phenoxy]piperidin-1-yl]ethyl]triazole-4-carboxamide Chemical compound FC(F)(F)C1=CC=CC(OC2CCN(CC2)C(=O)CNC(=O)C=2N=NN(C=2)C=2C(=CC=CC=2)C#N)=C1 VLZSMKGNKCKWGB-UHFFFAOYSA-N 0.000 claims description 4
- JDONNHWGOAKPSY-UHFFFAOYSA-N 1-morpholin-4-yltriazole-4-carboxylic acid Chemical compound N1=NC(C(=O)O)=CN1N1CCOCC1 JDONNHWGOAKPSY-UHFFFAOYSA-N 0.000 claims description 4
- YAYDMJNTBGROTD-UHFFFAOYSA-N chembl1528711 Chemical compound N1N=C(C(=O)O)C=C1C1=CC=C(O)C=C1 YAYDMJNTBGROTD-UHFFFAOYSA-N 0.000 claims description 4
- HEGYWIITYGSWIC-UHFFFAOYSA-N n-[2-[3-(2,5-difluorophenoxy)pyrrolidin-1-yl]-2-oxoethyl]-1-pyridin-3-yltriazole-4-carboxamide Chemical compound FC1=CC=C(F)C(OC2CN(CC2)C(=O)CNC(=O)C=2N=NN(C=2)C=2C=NC=CC=2)=C1 HEGYWIITYGSWIC-UHFFFAOYSA-N 0.000 claims description 4
- YBZAZJVFYNOKDB-UHFFFAOYSA-N n-[2-[4-(2,5-difluorophenoxy)piperidin-1-yl]-2-oxoethyl]-1-phenylimidazole-4-carboxamide Chemical class FC1=CC=C(F)C(OC2CCN(CC2)C(=O)CNC(=O)C=2N=CN(C=2)C=2C=CC=CC=2)=C1 YBZAZJVFYNOKDB-UHFFFAOYSA-N 0.000 claims description 4
- KSNATNDDQSJPIW-UHFFFAOYSA-N n-[2-[4-(2-chlorophenoxy)piperidin-1-yl]-2-oxoethyl]-1-phenylimidazole-4-carboxamide Chemical compound ClC1=CC=CC=C1OC1CCN(C(=O)CNC(=O)C=2N=CN(C=2)C=2C=CC=CC=2)CC1 KSNATNDDQSJPIW-UHFFFAOYSA-N 0.000 claims description 4
- QRXORACKJIXAMU-UHFFFAOYSA-N n-[2-[4-(2-chlorophenoxy)piperidin-1-yl]-2-oxoethyl]-1-phenyltriazole-4-carboxamide Chemical compound ClC1=CC=CC=C1OC1CCN(C(=O)CNC(=O)C=2N=NN(C=2)C=2C=CC=CC=2)CC1 QRXORACKJIXAMU-UHFFFAOYSA-N 0.000 claims description 4
- OCZMEMHUQZONON-UHFFFAOYSA-N n-[2-[4-(5-chloropyridin-3-yl)oxypiperidin-1-yl]-2-oxoethyl]-1-cyclopentyltriazole-4-carboxamide Chemical compound ClC1=CN=CC(OC2CCN(CC2)C(=O)CNC(=O)C=2N=NN(C=2)C2CCCC2)=C1 OCZMEMHUQZONON-UHFFFAOYSA-N 0.000 claims description 4
- PEUIQJVBBWBMSQ-UHFFFAOYSA-N n-[2-[4-(5-cyano-2-methylphenoxy)piperidin-1-yl]-2-oxoethyl]-1-pyridin-3-yltriazole-4-carboxamide Chemical compound CC1=CC=C(C#N)C=C1OC1CCN(C(=O)CNC(=O)C=2N=NN(C=2)C=2C=NC=CC=2)CC1 PEUIQJVBBWBMSQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- KOWRVFWZCLHEIU-UHFFFAOYSA-N 3-(3-hydroxyphenyl)-1h-pyrazole-5-carboxylic acid Chemical compound N1C(C(=O)O)=CC(C=2C=C(O)C=CC=2)=N1 KOWRVFWZCLHEIU-UHFFFAOYSA-N 0.000 claims description 3
- HOFZUBUICNNTOE-UHFFFAOYSA-N 3-[4-(2,3-dimethylanilino)piperidin-1-yl]-3-oxo-n-(4-phenylphenyl)propanamide Chemical compound CC1=CC=CC(NC2CCN(CC2)C(=O)CC(=O)NC=2C=CC(=CC=2)C=2C=CC=CC=2)=C1C HOFZUBUICNNTOE-UHFFFAOYSA-N 0.000 claims description 3
- XPXXYCCHDJLLLG-UHFFFAOYSA-N 3-[4-(2,4-dimethylanilino)piperidin-1-yl]-3-oxo-n-(4-phenylphenyl)propanamide Chemical compound CC1=CC(C)=CC=C1NC1CCN(C(=O)CC(=O)NC=2C=CC(=CC=2)C=2C=CC=CC=2)CC1 XPXXYCCHDJLLLG-UHFFFAOYSA-N 0.000 claims description 3
- BDOBLCDYWFTAGA-UHFFFAOYSA-N 3-[4-(2,5-difluorophenoxy)piperidin-1-yl]-3-oxo-n-(4-phenylphenyl)propanamide Chemical compound FC1=CC=C(F)C(OC2CCN(CC2)C(=O)CC(=O)NC=2C=CC(=CC=2)C=2C=CC=CC=2)=C1 BDOBLCDYWFTAGA-UHFFFAOYSA-N 0.000 claims description 3
- RNTFBCPBIIECHG-UHFFFAOYSA-N 3-[4-(2,5-dimethylanilino)piperidin-1-yl]-3-oxo-n-(4-phenylphenyl)propanamide Chemical compound CC1=CC=C(C)C(NC2CCN(CC2)C(=O)CC(=O)NC=2C=CC(=CC=2)C=2C=CC=CC=2)=C1 RNTFBCPBIIECHG-UHFFFAOYSA-N 0.000 claims description 3
- PVMAVVKCBJVOIS-UHFFFAOYSA-N 3-[4-(2-aminophenoxy)piperidin-1-yl]-3-oxo-n-(4-phenylphenyl)propanamide Chemical compound NC1=CC=CC=C1OC1CCN(C(=O)CC(=O)NC=2C=CC(=CC=2)C=2C=CC=CC=2)CC1 PVMAVVKCBJVOIS-UHFFFAOYSA-N 0.000 claims description 3
- LMTFETKUEHTGOQ-UHFFFAOYSA-N 3-[4-(2-bromoanilino)piperidin-1-yl]-3-oxo-n-(4-phenylphenyl)propanamide Chemical compound BrC1=CC=CC=C1NC1CCN(C(=O)CC(=O)NC=2C=CC(=CC=2)C=2C=CC=CC=2)CC1 LMTFETKUEHTGOQ-UHFFFAOYSA-N 0.000 claims description 3
- VAEWAVHUBWTGSH-UHFFFAOYSA-N 3-[4-(2-bromoanilino)piperidin-1-yl]-3-oxo-n-(6-phenylpyridin-3-yl)propanamide Chemical compound BrC1=CC=CC=C1NC1CCN(C(=O)CC(=O)NC=2C=NC(=CC=2)C=2C=CC=CC=2)CC1 VAEWAVHUBWTGSH-UHFFFAOYSA-N 0.000 claims description 3
- UUIGUCKWXJLEEO-UHFFFAOYSA-N 3-[4-(2-bromophenoxy)piperidin-1-yl]-3-oxo-n-(4-phenylphenyl)propanamide Chemical compound BrC1=CC=CC=C1OC1CCN(C(=O)CC(=O)NC=2C=CC(=CC=2)C=2C=CC=CC=2)CC1 UUIGUCKWXJLEEO-UHFFFAOYSA-N 0.000 claims description 3
- QGWBZLVWAMPTAZ-UHFFFAOYSA-N 3-[4-(2-bromophenyl)sulfanylpiperidin-1-yl]-3-oxo-n-(4-phenylphenyl)propanamide Chemical compound BrC1=CC=CC=C1SC1CCN(C(=O)CC(=O)NC=2C=CC(=CC=2)C=2C=CC=CC=2)CC1 QGWBZLVWAMPTAZ-UHFFFAOYSA-N 0.000 claims description 3
- XFCKOIMBVJSVGH-UHFFFAOYSA-N 3-[4-(2-bromophenyl)sulfanylpiperidin-1-yl]-3-oxo-n-(6-phenylpyridin-3-yl)propanamide Chemical compound BrC1=CC=CC=C1SC1CCN(C(=O)CC(=O)NC=2C=NC(=CC=2)C=2C=CC=CC=2)CC1 XFCKOIMBVJSVGH-UHFFFAOYSA-N 0.000 claims description 3
- GFIFKGLZEGKMTK-UHFFFAOYSA-N 3-[4-(2-chloro-5-fluorophenoxy)piperidin-1-yl]-3-oxo-n-(4-phenylphenyl)propanamide Chemical compound FC1=CC=C(Cl)C(OC2CCN(CC2)C(=O)CC(=O)NC=2C=CC(=CC=2)C=2C=CC=CC=2)=C1 GFIFKGLZEGKMTK-UHFFFAOYSA-N 0.000 claims description 3
- BDNUNADUZOTDKX-UHFFFAOYSA-N 3-[4-(2-chloro-5-fluorophenoxy)piperidin-1-yl]-3-oxo-n-(5-phenylpyridin-2-yl)propanamide Chemical compound FC1=CC=C(Cl)C(OC2CCN(CC2)C(=O)CC(=O)NC=2N=CC(=CC=2)C=2C=CC=CC=2)=C1 BDNUNADUZOTDKX-UHFFFAOYSA-N 0.000 claims description 3
- XYMHUTNQALHNMM-UHFFFAOYSA-N 3-[4-(2-chloro-5-fluorophenoxy)piperidin-1-yl]-3-oxo-n-(6-phenylpyridin-3-yl)propanamide Chemical compound FC1=CC=C(Cl)C(OC2CCN(CC2)C(=O)CC(=O)NC=2C=NC(=CC=2)C=2C=CC=CC=2)=C1 XYMHUTNQALHNMM-UHFFFAOYSA-N 0.000 claims description 3
- WCAVUEHNHOEMSX-UHFFFAOYSA-N 3-[4-(2-chloroanilino)piperidin-1-yl]-3-oxo-n-(5-phenyl-1,3-thiazol-2-yl)propanamide Chemical compound ClC1=CC=CC=C1NC1CCN(C(=O)CC(=O)NC=2SC(=CN=2)C=2C=CC=CC=2)CC1 WCAVUEHNHOEMSX-UHFFFAOYSA-N 0.000 claims description 3
- LYZYOMIFKVOTRA-UHFFFAOYSA-N 3-[4-(2-chloroanilino)piperidin-1-yl]-3-oxo-n-(6-phenylpyridin-3-yl)propanamide Chemical compound ClC1=CC=CC=C1NC1CCN(C(=O)CC(=O)NC=2C=NC(=CC=2)C=2C=CC=CC=2)CC1 LYZYOMIFKVOTRA-UHFFFAOYSA-N 0.000 claims description 3
- BKKAQJXEIVTPGM-UHFFFAOYSA-N 3-[4-(2-chlorophenoxy)piperidin-1-yl]-3-oxo-n-(3-phenyl-1,2,4-thiadiazol-5-yl)propanamide Chemical compound ClC1=CC=CC=C1OC1CCN(C(=O)CC(=O)NC=2SN=C(N=2)C=2C=CC=CC=2)CC1 BKKAQJXEIVTPGM-UHFFFAOYSA-N 0.000 claims description 3
- DUIQSVQAWKATIR-UHFFFAOYSA-N 3-[4-(2-chlorophenoxy)piperidin-1-yl]-3-oxo-n-(5-phenyl-1,3-thiazol-2-yl)propanamide Chemical compound ClC1=CC=CC=C1OC1CCN(C(=O)CC(=O)NC=2SC(=CN=2)C=2C=CC=CC=2)CC1 DUIQSVQAWKATIR-UHFFFAOYSA-N 0.000 claims description 3
- BBFBPVOSCMRHAO-UHFFFAOYSA-N 3-[4-(2-chlorophenoxy)piperidin-1-yl]-3-oxo-n-(6-phenylpyridin-3-yl)propanamide Chemical compound ClC1=CC=CC=C1OC1CCN(C(=O)CC(=O)NC=2C=NC(=CC=2)C=2C=CC=CC=2)CC1 BBFBPVOSCMRHAO-UHFFFAOYSA-N 0.000 claims description 3
- HEDUOWWFDPUAQS-UHFFFAOYSA-N 3-[4-(2-chlorophenoxy)piperidin-1-yl]-n-[4-(1,2,4-oxadiazol-3-yl)phenyl]-3-oxopropanamide Chemical compound ClC1=CC=CC=C1OC1CCN(C(=O)CC(=O)NC=2C=CC(=CC=2)C2=NOC=N2)CC1 HEDUOWWFDPUAQS-UHFFFAOYSA-N 0.000 claims description 3
- ALWOANMIKBRIPL-UHFFFAOYSA-N 3-[4-(2-chlorophenyl)sulfanylpiperidin-1-yl]-3-oxo-n-(6-phenylpyridin-3-yl)propanamide Chemical compound ClC1=CC=CC=C1SC1CCN(C(=O)CC(=O)NC=2C=NC(=CC=2)C=2C=CC=CC=2)CC1 ALWOANMIKBRIPL-UHFFFAOYSA-N 0.000 claims description 3
- ODSKZIKVMYRKMD-UHFFFAOYSA-N 3-[4-(2-methylanilino)piperidin-1-yl]-3-oxo-n-(4-phenylphenyl)propanamide Chemical compound CC1=CC=CC=C1NC1CCN(C(=O)CC(=O)NC=2C=CC(=CC=2)C=2C=CC=CC=2)CC1 ODSKZIKVMYRKMD-UHFFFAOYSA-N 0.000 claims description 3
- CTKAWQIIQDLYMX-UHFFFAOYSA-N 3-[4-(2-methylanilino)piperidin-1-yl]-3-oxo-n-(6-phenylpyridin-3-yl)propanamide Chemical compound CC1=CC=CC=C1NC1CCN(C(=O)CC(=O)NC=2C=NC(=CC=2)C=2C=CC=CC=2)CC1 CTKAWQIIQDLYMX-UHFFFAOYSA-N 0.000 claims description 3
- DAWLJPOZGTYCCA-UHFFFAOYSA-N 3-[4-(2-nitrophenoxy)piperidin-1-yl]-3-oxo-n-(4-phenylphenyl)propanamide Chemical compound [O-][N+](=O)C1=CC=CC=C1OC1CCN(C(=O)CC(=O)NC=2C=CC(=CC=2)C=2C=CC=CC=2)CC1 DAWLJPOZGTYCCA-UHFFFAOYSA-N 0.000 claims description 3
- ANILIVZLWJKPRD-UHFFFAOYSA-N 3-[4-(2-tert-butylanilino)piperidin-1-yl]-3-oxo-n-(4-phenylphenyl)propanamide Chemical compound CC(C)(C)C1=CC=CC=C1NC1CCN(C(=O)CC(=O)NC=2C=CC(=CC=2)C=2C=CC=CC=2)CC1 ANILIVZLWJKPRD-UHFFFAOYSA-N 0.000 claims description 3
- NXRWUHBEAUHMOQ-UHFFFAOYSA-N 3-oxo-n-(6-phenylpyridin-3-yl)-3-[4-[2-(trifluoromethyl)anilino]piperidin-1-yl]propanamide Chemical compound FC(F)(F)C1=CC=CC=C1NC1CCN(C(=O)CC(=O)NC=2C=NC(=CC=2)C=2C=CC=CC=2)CC1 NXRWUHBEAUHMOQ-UHFFFAOYSA-N 0.000 claims description 3
- GYELPMCREZETQR-UHFFFAOYSA-N 3-oxo-n-(6-phenylpyridin-3-yl)-3-[4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl]propanamide Chemical compound FC(F)(F)C1=CC=CC=C1OC1CCN(C(=O)CC(=O)NC=2C=NC(=CC=2)C=2C=CC=CC=2)CC1 GYELPMCREZETQR-UHFFFAOYSA-N 0.000 claims description 3
- OVJSTHBDUBWNDW-UHFFFAOYSA-N 3-oxo-n-(6-phenylpyridin-3-yl)-3-[4-[2-(trifluoromethyl)phenyl]sulfanylpiperidin-1-yl]propanamide Chemical compound FC(F)(F)C1=CC=CC=C1SC1CCN(C(=O)CC(=O)NC=2C=NC(=CC=2)C=2C=CC=CC=2)CC1 OVJSTHBDUBWNDW-UHFFFAOYSA-N 0.000 claims description 3
- STCWFUZPIZNCNS-UHFFFAOYSA-N 4-anilino-n-[2-[4-(2-bromoanilino)piperidin-1-yl]-2-oxoethyl]benzamide Chemical compound BrC1=CC=CC=C1NC1CCN(C(=O)CNC(=O)C=2C=CC(NC=3C=CC=CC=3)=CC=2)CC1 STCWFUZPIZNCNS-UHFFFAOYSA-N 0.000 claims description 3
- IIVSFXAFASMDEP-UHFFFAOYSA-N 4-anilino-n-[2-[4-(2-bromophenoxy)piperidin-1-yl]-2-oxoethyl]benzamide Chemical compound BrC1=CC=CC=C1OC1CCN(C(=O)CNC(=O)C=2C=CC(NC=3C=CC=CC=3)=CC=2)CC1 IIVSFXAFASMDEP-UHFFFAOYSA-N 0.000 claims description 3
- HDPDYSKMTICOON-UHFFFAOYSA-N 4-anilino-n-[2-[4-[n-methyl-2-(trifluoromethyl)anilino]piperidin-1-yl]-2-oxoethyl]benzamide Chemical compound C=1C=CC=C(C(F)(F)F)C=1N(C)C(CC1)CCN1C(=O)CNC(=O)C(C=C1)=CC=C1NC1=CC=CC=C1 HDPDYSKMTICOON-UHFFFAOYSA-N 0.000 claims description 3
- YEMIVSHSZFWHFW-UHFFFAOYSA-N 4-anilino-n-[2-oxo-2-[4-[2-(trifluoromethyl)anilino]piperidin-1-yl]ethyl]benzamide Chemical compound FC(F)(F)C1=CC=CC=C1NC1CCN(C(=O)CNC(=O)C=2C=CC(NC=3C=CC=CC=3)=CC=2)CC1 YEMIVSHSZFWHFW-UHFFFAOYSA-N 0.000 claims description 3
- AMBDRXRCOGOEHY-UHFFFAOYSA-N 6-anilino-n-[2-[4-(2-chloroanilino)piperidin-1-yl]-2-oxoethyl]pyridine-3-carboxamide Chemical compound ClC1=CC=CC=C1NC1CCN(C(=O)CNC(=O)C=2C=NC(NC=3C=CC=CC=3)=CC=2)CC1 AMBDRXRCOGOEHY-UHFFFAOYSA-N 0.000 claims description 3
- CVCPMHBFYCTWQH-UHFFFAOYSA-N 6-anilino-n-[2-[4-(2-chlorophenoxy)piperidin-1-yl]-2-oxoethyl]pyridine-3-carboxamide Chemical compound ClC1=CC=CC=C1OC1CCN(C(=O)CNC(=O)C=2C=NC(NC=3C=CC=CC=3)=CC=2)CC1 CVCPMHBFYCTWQH-UHFFFAOYSA-N 0.000 claims description 3
- 101710159293 Acyl-CoA desaturase 1 Proteins 0.000 claims description 3
- JJQRBLLPQYFXHQ-UHFFFAOYSA-N N-[2-[4-(2-chloroanilino)piperidin-1-yl]-2-oxoethyl]-3-(2-hydroxyphenyl)-1H-pyrazole-5-carboxamide Chemical compound OC1=CC=CC=C1C1=CC(C(=O)NCC(=O)N2CCC(CC2)NC=2C(=CC=CC=2)Cl)=NN1 JJQRBLLPQYFXHQ-UHFFFAOYSA-N 0.000 claims description 3
- SYMQLTABFSPTCQ-UHFFFAOYSA-N N-[2-[4-(2-chloroanilino)piperidin-1-yl]-2-oxoethyl]-3-(4-hydroxyphenyl)-1H-pyrazole-5-carboxamide Chemical compound C1=CC(O)=CC=C1C1=CC(C(=O)NCC(=O)N2CCC(CC2)NC=2C(=CC=CC=2)Cl)=NN1 SYMQLTABFSPTCQ-UHFFFAOYSA-N 0.000 claims description 3
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- COCQAMZMHQHXGO-UHFFFAOYSA-N n-[2-[4-(2-chlorophenoxy)piperidin-1-yl]-2-oxoethyl]-3-(2-phenylmethoxyphenyl)-1h-pyrazole-5-carboxamide Chemical compound ClC1=CC=CC=C1OC1CCN(C(=O)CNC(=O)C2=NNC(=C2)C=2C(=CC=CC=2)OCC=2C=CC=CC=2)CC1 COCQAMZMHQHXGO-UHFFFAOYSA-N 0.000 description 1
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- KVBGVZZKJNLNJU-UHFFFAOYSA-M naphthalene-2-sulfonate Chemical compound C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-M 0.000 description 1
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- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- XDUHQPOXLUAVEE-BPMMELMSSA-N oleoyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CCCCCCC\C=C/CCCCCCCC)O[C@H]1N1C2=NC=NC(N)=C2N=C1 XDUHQPOXLUAVEE-BPMMELMSSA-N 0.000 description 1
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- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
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- 230000036573 scar formation Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
- 229960002218 sodium chlorite Drugs 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- LZCVVMQABORALM-UHFFFAOYSA-N spiro[2.5]octyl Chemical group [CH]1CC11CCCCC1 LZCVVMQABORALM-UHFFFAOYSA-N 0.000 description 1
- GAJDDVONBAWAGB-UHFFFAOYSA-N spiro[2.6]nonyl Chemical group [CH]1CC11CCCCCC1 GAJDDVONBAWAGB-UHFFFAOYSA-N 0.000 description 1
- LMUMMJCCZMWLEN-UHFFFAOYSA-N spiro[3.3]heptyl Chemical group [CH]1CCC11CCC1 LMUMMJCCZMWLEN-UHFFFAOYSA-N 0.000 description 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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- 229960001367 tartaric acid Drugs 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- BSKBAIKXWXHBKK-UHFFFAOYSA-N tert-butyl 4-(2,5-difluorophenoxy)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=CC(F)=CC=C1F BSKBAIKXWXHBKK-UHFFFAOYSA-N 0.000 description 1
- KMBSMBPVRYKLIA-UHFFFAOYSA-N tert-butyl 4-(2-chloro-5-fluorophenoxy)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=CC(F)=CC=C1Cl KMBSMBPVRYKLIA-UHFFFAOYSA-N 0.000 description 1
- YBZRUUFGFIXTCZ-UHFFFAOYSA-N tert-butyl 4-(2-chloro-n-methylanilino)piperidine-1-carboxylate Chemical compound C=1C=CC=C(Cl)C=1N(C)C1CCN(C(=O)OC(C)(C)C)CC1 YBZRUUFGFIXTCZ-UHFFFAOYSA-N 0.000 description 1
- QMADZUIDYBWTFY-UHFFFAOYSA-N tert-butyl 4-(2-chlorophenoxy)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=CC=CC=C1Cl QMADZUIDYBWTFY-UHFFFAOYSA-N 0.000 description 1
- HOFQGKPYMSEWGC-UHFFFAOYSA-N tert-butyl 4-(2-chlorophenyl)sulfanylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1SC1=CC=CC=C1Cl HOFQGKPYMSEWGC-UHFFFAOYSA-N 0.000 description 1
- BOGXZBVKQDEROE-UHFFFAOYSA-N tert-butyl 4-(2-tert-butylanilino)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1NC1=CC=CC=C1C(C)(C)C BOGXZBVKQDEROE-UHFFFAOYSA-N 0.000 description 1
- NMYLUTZGNZLFET-UHFFFAOYSA-N tert-butyl 4-[2-(trifluoromethyl)phenoxy]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=CC=CC=C1C(F)(F)F NMYLUTZGNZLFET-UHFFFAOYSA-N 0.000 description 1
- PBEAHUOAXQPWRU-UHFFFAOYSA-N tert-butyl 4-[n-methyl-2-(trifluoromethyl)anilino]piperidine-1-carboxylate Chemical compound C=1C=CC=C(C(F)(F)F)C=1N(C)C1CCN(C(=O)OC(C)(C)C)CC1 PBEAHUOAXQPWRU-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 238000011285 therapeutic regimen Methods 0.000 description 1
- 125000005302 thiazolylmethyl group Chemical group [H]C1=C([H])N=C(S1)C([H])([H])* 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 1
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- 201000010875 transient cerebral ischemia Diseases 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 208000016261 weight loss Diseases 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D401/02—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 two hetero rings
- C07D401/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN575KO2008 | 2008-03-20 | ||
| IN575/KOL/2008 | 2008-03-20 | ||
| US4948008P | 2008-05-01 | 2008-05-01 | |
| US61/049,480 | 2008-05-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20100134680A true KR20100134680A (ko) | 2010-12-23 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020107023415A Ceased KR20100134680A (ko) | 2008-03-20 | 2009-03-20 | 스테아로일-coa 불포화효소의 저해물질로서 신규한 피페리딘 유도체 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US8129376B2 (https=) |
| EP (1) | EP2268143A4 (https=) |
| JP (1) | JP2011518774A (https=) |
| KR (1) | KR20100134680A (https=) |
| CN (1) | CN102036558A (https=) |
| AU (1) | AU2009225441B2 (https=) |
| BR (1) | BRPI0909183A2 (https=) |
| CA (1) | CA2719000A1 (https=) |
| IL (1) | IL208232A0 (https=) |
| MX (1) | MX2010010241A (https=) |
| NZ (1) | NZ588633A (https=) |
| RU (1) | RU2010142937A (https=) |
| WO (1) | WO2009117676A2 (https=) |
| ZA (1) | ZA201007252B (https=) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8586571B2 (en) | 2007-10-18 | 2013-11-19 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
| US8642583B2 (en) * | 2008-10-30 | 2014-02-04 | Janssen Pharmaceutica Nv | Serotonin receptor modulators |
| MX336731B (es) | 2010-01-28 | 2016-01-28 | Harvard College | Composiciones y metodos para potenciar la actividad de proteasoma. |
| WO2012007500A2 (de) | 2010-07-15 | 2012-01-19 | Bayer Cropscience Ag | Neue heterocyclische verbindungen als schädlingsbekämpfungsmittel |
| DK2707101T3 (da) | 2011-05-12 | 2019-05-13 | Proteostasis Therapeutics Inc | Proteostaseregulatorer |
| NO2686520T3 (https=) | 2011-06-06 | 2018-03-17 | ||
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| US20090239810A1 (en) | 2009-09-24 |
| WO2009117676A3 (en) | 2010-01-07 |
| BRPI0909183A2 (pt) | 2015-08-25 |
| ZA201007252B (en) | 2011-12-28 |
| AU2009225441A1 (en) | 2009-09-24 |
| EP2268143A2 (en) | 2011-01-05 |
| RU2010142937A (ru) | 2012-04-27 |
| MX2010010241A (es) | 2010-12-06 |
| EP2268143A4 (en) | 2012-06-27 |
| AU2009225441B2 (en) | 2012-12-13 |
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