JP2008524244A5 - - Google Patents
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- JP2008524244A5 JP2008524244A5 JP2007546949A JP2007546949A JP2008524244A5 JP 2008524244 A5 JP2008524244 A5 JP 2008524244A5 JP 2007546949 A JP2007546949 A JP 2007546949A JP 2007546949 A JP2007546949 A JP 2007546949A JP 2008524244 A5 JP2008524244 A5 JP 2008524244A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- hetero
- cycloalkyl
- bicycloaryl
- aryl
- 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.)
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- 125000000217 alkyl group Chemical group 0.000 claims 819
- -1 nitro, carbonyl Chemical group 0.000 claims 470
- 125000005842 heteroatom Chemical group 0.000 claims 453
- 125000000753 cycloalkyl group Chemical group 0.000 claims 307
- 125000001072 heteroaryl group Chemical group 0.000 claims 286
- 150000001602 bicycloalkyls Chemical group 0.000 claims 273
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 262
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 231
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 228
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 165
- 125000003118 aryl group Chemical group 0.000 claims 158
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 139
- 229910052739 hydrogen Inorganic materials 0.000 claims 133
- 239000001257 hydrogen Substances 0.000 claims 133
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 133
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims 131
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 100
- 125000004104 aryloxy group Chemical group 0.000 claims 88
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 88
- 125000003545 alkoxy group Chemical group 0.000 claims 86
- 125000003282 alkyl amino group Chemical group 0.000 claims 86
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 72
- 229940124530 sulfonamide Drugs 0.000 claims 65
- 150000003456 sulfonamides Chemical class 0.000 claims 65
- 150000001875 compounds Chemical class 0.000 claims 62
- 239000000203 mixture Substances 0.000 claims 11
- 239000008194 pharmaceutical composition Substances 0.000 claims 9
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 7
- 201000010099 disease Diseases 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 4
- 125000005059 halophenyl group Chemical group 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- KFPPCXCRXLVUSU-UHFFFAOYSA-N 3-chloro-n-[4-(1-hydroxy-2-pyrimidin-4-ylethyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(C(O)CC=2N=CN=CC=2)=CS1 KFPPCXCRXLVUSU-UHFFFAOYSA-N 0.000 claims 2
- VPBQKCAXFSUGHX-UHFFFAOYSA-N 3-chloro-n-[4-[(2-chloropyridin-3-yl)-hydroxymethyl]-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(C(O)C=2C(=NC=CC=2)Cl)=CS1 VPBQKCAXFSUGHX-UHFFFAOYSA-N 0.000 claims 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims 2
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims 2
- 125000002431 aminoalkoxy group Chemical group 0.000 claims 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims 2
- YDVJBLJCSLVMSY-UHFFFAOYSA-N carbamoyl cyanide Chemical class NC(=O)C#N YDVJBLJCSLVMSY-UHFFFAOYSA-N 0.000 claims 2
- 125000004802 cyanophenyl group Chemical group 0.000 claims 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- 239000012669 liquid formulation Substances 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 239000005022 packaging material Substances 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000003944 tolyl group Chemical group 0.000 claims 2
- PHKCXCSOILQNJY-UHFFFAOYSA-N 2-chloro-4-[3-(dimethylamino)propyl]-n-[4-(2-ethyl-2-hydroxybutyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CCC(O)(CC)CC1=CSC(NS(=O)(=O)C=2C(=CC(CCCN(C)C)=CC=2)Cl)=N1 PHKCXCSOILQNJY-UHFFFAOYSA-N 0.000 claims 1
- LUCQCNONRGGAFF-UHFFFAOYSA-N 2-chloro-4-[4-(dimethylamino)butyl]-n-[4-(2-ethyl-2-hydroxybutyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CCC(O)(CC)CC1=CSC(NS(=O)(=O)C=2C(=CC(CCCCN(C)C)=CC=2)Cl)=N1 LUCQCNONRGGAFF-UHFFFAOYSA-N 0.000 claims 1
- GNBJPDZEVGQCLW-UHFFFAOYSA-N 2-chloro-n-[4-(2-ethyl-2-hydroxybutyl)-1,3-thiazol-2-yl]-4-(3-morpholin-4-ylpropyl)benzenesulfonamide Chemical compound CCC(O)(CC)CC1=CSC(NS(=O)(=O)C=2C(=CC(CCCN3CCOCC3)=CC=2)Cl)=N1 GNBJPDZEVGQCLW-UHFFFAOYSA-N 0.000 claims 1
- LMCXALCBMPZMFT-UHFFFAOYSA-N 2-chloro-n-[4-(2-ethyl-2-hydroxybutyl)-1,3-thiazol-2-yl]-4-(4-morpholin-4-ylbutyl)benzenesulfonamide Chemical compound CCC(O)(CC)CC1=CSC(NS(=O)(=O)C=2C(=CC(CCCCN3CCOCC3)=CC=2)Cl)=N1 LMCXALCBMPZMFT-UHFFFAOYSA-N 0.000 claims 1
- JEHQGKQGBCZUKA-UHFFFAOYSA-N 2-fluoro-n-[4-(3-hydroxypentan-3-yl)-1,3-thiazol-2-yl]-5-methylbenzenesulfonamide Chemical compound CCC(O)(CC)C1=CSC(NS(=O)(=O)C=2C(=CC=C(C)C=2)F)=N1 JEHQGKQGBCZUKA-UHFFFAOYSA-N 0.000 claims 1
- BJDWYDVMERXVHB-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-[(2-methylphenyl)methyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=CC=CC=C1CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 BJDWYDVMERXVHB-UHFFFAOYSA-N 0.000 claims 1
- BYXFCRIHQDHIAK-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-[(3-methylphenyl)methyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=CC=CC(CC=2N=C(NS(=O)(=O)C=3C(=C(Cl)C=CC=3)C)SC=2)=C1 BYXFCRIHQDHIAK-UHFFFAOYSA-N 0.000 claims 1
- YDPAQELDBKPASA-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-[(4-methyloxan-4-yl)methyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CC2(C)CCOCC2)=CS1 YDPAQELDBKPASA-UHFFFAOYSA-N 0.000 claims 1
- AWKIRIFWOJWVBO-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-[[3-(trifluoromethyl)phenyl]methyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CC=2C=C(C=CC=2)C(F)(F)F)=CS1 AWKIRIFWOJWVBO-UHFFFAOYSA-N 0.000 claims 1
- CPIHTKBKMBJTNQ-UHFFFAOYSA-N 3-chloro-4-[2-(dimethylamino)ethoxy]-n-[4-(2-ethyl-2-hydroxybutyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CCC(O)(CC)CC1=CSC(NS(=O)(=O)C=2C=C(Cl)C(OCCN(C)C)=CC=2)=N1 CPIHTKBKMBJTNQ-UHFFFAOYSA-N 0.000 claims 1
- AVFXATVCYLCYFE-UHFFFAOYSA-N 3-chloro-4-[2-(dimethylamino)ethoxy]-n-[4-[(1-hydroxycyclohexyl)methyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C1=C(Cl)C(OCCN(C)C)=CC=C1S(=O)(=O)NC1=NC(CC2(O)CCCCC2)=CS1 AVFXATVCYLCYFE-UHFFFAOYSA-N 0.000 claims 1
- QHIXYOXOJBMSTB-UHFFFAOYSA-N 3-chloro-4-[2-(dimethylamino)ethoxy]-n-[4-[(1-hydroxycyclopentyl)methyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C1=C(Cl)C(OCCN(C)C)=CC=C1S(=O)(=O)NC1=NC(CC2(O)CCCC2)=CS1 QHIXYOXOJBMSTB-UHFFFAOYSA-N 0.000 claims 1
- JXTLNGMJRGZROG-UHFFFAOYSA-N 3-chloro-4-[3-(dimethylamino)propoxy]-n-[4-(2-ethyl-2-hydroxybutyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CCC(O)(CC)CC1=CSC(NS(=O)(=O)C=2C=C(Cl)C(OCCCN(C)C)=CC=2)=N1 JXTLNGMJRGZROG-UHFFFAOYSA-N 0.000 claims 1
- ZPHQEQHBZRFYRL-UHFFFAOYSA-N 3-chloro-5-[2-(dimethylamino)ethoxy]-n-[4-(2-ethyl-2-hydroxybutyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CCC(O)(CC)CC1=CSC(NS(=O)(=O)C=2C=C(OCCN(C)C)C=C(Cl)C=2)=N1 ZPHQEQHBZRFYRL-UHFFFAOYSA-N 0.000 claims 1
- VORJWBYARBJIJW-UHFFFAOYSA-N 3-chloro-5-[3-(dimethylamino)propoxy]-n-[4-(2-ethyl-2-hydroxybutyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CCC(O)(CC)CC1=CSC(NS(=O)(=O)C=2C=C(OCCCN(C)C)C=C(Cl)C=2)=N1 VORJWBYARBJIJW-UHFFFAOYSA-N 0.000 claims 1
- LWWBYWVWSIFAPY-UHFFFAOYSA-N 3-chloro-N-[4-[1-hydroxy-2-(1H-pyrazol-5-yl)ethyl]-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(C(O)CC=2NN=CC=2)=CS1 LWWBYWVWSIFAPY-UHFFFAOYSA-N 0.000 claims 1
- WXYKPGAUQXEQRE-UHFFFAOYSA-N 3-chloro-n-[4-(1-hydroxy-2-methylpropyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC(C)C(O)C1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 WXYKPGAUQXEQRE-UHFFFAOYSA-N 0.000 claims 1
- PTCYNDAAMFWLAJ-UHFFFAOYSA-N 3-chloro-n-[4-(1-hydroxy-2-phenylethyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(C(O)CC=2C=CC=CC=2)=CS1 PTCYNDAAMFWLAJ-UHFFFAOYSA-N 0.000 claims 1
- LFZDLJDTBDTGGX-UHFFFAOYSA-N 3-chloro-n-[4-(1-hydroxy-3-phenylpropyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(C(O)CCC=2C=CC=CC=2)=CS1 LFZDLJDTBDTGGX-UHFFFAOYSA-N 0.000 claims 1
- WGEUQASJGZRSSF-UHFFFAOYSA-N 3-chloro-n-[4-(1-hydroxybutyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CCCC(O)C1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 WGEUQASJGZRSSF-UHFFFAOYSA-N 0.000 claims 1
- RISIGWARYNDZAP-UHFFFAOYSA-N 3-chloro-n-[4-(1-hydroxycyclopentyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(C2(O)CCCC2)=CS1 RISIGWARYNDZAP-UHFFFAOYSA-N 0.000 claims 1
- OXVMERNZHQPPHW-UHFFFAOYSA-N 3-chloro-n-[4-(1-hydroxycyclopropyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(C2(O)CC2)=CS1 OXVMERNZHQPPHW-UHFFFAOYSA-N 0.000 claims 1
- JQXKSTUAUGAUDM-UHFFFAOYSA-N 3-chloro-n-[4-(1-hydroxyethyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC(O)C1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 JQXKSTUAUGAUDM-UHFFFAOYSA-N 0.000 claims 1
- OOZVOYCUPAZZAH-UHFFFAOYSA-N 3-chloro-n-[4-(1-hydroxypropyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CCC(O)C1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 OOZVOYCUPAZZAH-UHFFFAOYSA-N 0.000 claims 1
- WONHMKOHTMYBFH-UHFFFAOYSA-N 3-chloro-n-[4-(2-cyclopentyl-2-hydroxyethyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CC(O)C2CCCC2)=CS1 WONHMKOHTMYBFH-UHFFFAOYSA-N 0.000 claims 1
- NDCAZJSKDRJZGP-UHFFFAOYSA-N 3-chloro-n-[4-(2-cyclopropyl-2-hydroxyethyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CC(O)C2CC2)=CS1 NDCAZJSKDRJZGP-UHFFFAOYSA-N 0.000 claims 1
- ODXTXZOKLBAFPN-UHFFFAOYSA-N 3-chloro-n-[4-(2-ethyl-2-hydroxybutyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CCC(O)(CC)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 ODXTXZOKLBAFPN-UHFFFAOYSA-N 0.000 claims 1
- NONIGDXHMHWZOB-UHFFFAOYSA-N 3-chloro-n-[4-(2-ethyl-2-hydroxybutyl)-1,3-thiazol-2-yl]-4-(2-morpholin-4-ylethoxy)benzenesulfonamide Chemical compound CCC(O)(CC)CC1=CSC(NS(=O)(=O)C=2C=C(Cl)C(OCCN3CCOCC3)=CC=2)=N1 NONIGDXHMHWZOB-UHFFFAOYSA-N 0.000 claims 1
- JCKGOHNDNXKVHW-UHFFFAOYSA-N 3-chloro-n-[4-(2-ethyl-2-hydroxybutyl)-1,3-thiazol-2-yl]-4-(3-morpholin-4-ylpropoxy)benzenesulfonamide Chemical compound CCC(O)(CC)CC1=CSC(NS(=O)(=O)C=2C=C(Cl)C(OCCCN3CCOCC3)=CC=2)=N1 JCKGOHNDNXKVHW-UHFFFAOYSA-N 0.000 claims 1
- GRKHWHBZFTXMIY-UHFFFAOYSA-N 3-chloro-n-[4-(2-ethyl-2-hydroxybutyl)-1,3-thiazol-2-yl]-4-fluorobenzenesulfonamide Chemical compound CCC(O)(CC)CC1=CSC(NS(=O)(=O)C=2C=C(Cl)C(F)=CC=2)=N1 GRKHWHBZFTXMIY-UHFFFAOYSA-N 0.000 claims 1
- RIWRJRICENUWTD-UHFFFAOYSA-N 3-chloro-n-[4-(2-ethyl-2-hydroxybutyl)-1,3-thiazol-2-yl]-5-(3-morpholin-4-ylpropoxy)benzenesulfonamide Chemical compound CCC(O)(CC)CC1=CSC(NS(=O)(=O)C=2C=C(OCCCN3CCOCC3)C=C(Cl)C=2)=N1 RIWRJRICENUWTD-UHFFFAOYSA-N 0.000 claims 1
- DRMWTNSIGNAOTC-UHFFFAOYSA-N 3-chloro-n-[4-(2-hydroxy-2-phenylethyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CC(O)C=2C=CC=CC=2)=CS1 DRMWTNSIGNAOTC-UHFFFAOYSA-N 0.000 claims 1
- DXOMSFPNRSUXJH-UHFFFAOYSA-N 3-chloro-n-[4-(2-hydroxy-2-propylpentyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CCCC(O)(CCC)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 DXOMSFPNRSUXJH-UHFFFAOYSA-N 0.000 claims 1
- PCYGOSPNHRSWFU-UHFFFAOYSA-N 3-chloro-n-[4-(2-hydroxy-3,3-dimethylbutyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CC(O)C(C)(C)C)=CS1 PCYGOSPNHRSWFU-UHFFFAOYSA-N 0.000 claims 1
- ZJOGOXKVOUFTON-UHFFFAOYSA-N 3-chloro-n-[4-(2-hydroxy-3-methylbutyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC(C)C(O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 ZJOGOXKVOUFTON-UHFFFAOYSA-N 0.000 claims 1
- HGIQMOYTSUWTTL-UHFFFAOYSA-N 3-chloro-n-[4-(2-hydroxy-3-phenylpropyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CC(O)CC=2C=CC=CC=2)=CS1 HGIQMOYTSUWTTL-UHFFFAOYSA-N 0.000 claims 1
- LFJJHRMSUMWSSR-UHFFFAOYSA-N 3-chloro-n-[4-(2-hydroxy-3-pyridazin-3-ylpropyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CC(O)CC=2N=NC=CC=2)=CS1 LFJJHRMSUMWSSR-UHFFFAOYSA-N 0.000 claims 1
- CMOODWGEPYZOMF-UHFFFAOYSA-N 3-chloro-n-[4-(2-hydroxy-3-pyrimidin-4-ylpropyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CC(O)CC=2N=CN=CC=2)=CS1 CMOODWGEPYZOMF-UHFFFAOYSA-N 0.000 claims 1
- WFPKCUVDRJYBTL-UHFFFAOYSA-N 3-chloro-n-[4-(2-hydroxybutyl)-1,3-thiazol-2-yl]-4-(2-morpholin-4-ylethoxy)benzenesulfonamide Chemical compound CCC(O)CC1=CSC(NS(=O)(=O)C=2C=C(Cl)C(OCCN3CCOCC3)=CC=2)=N1 WFPKCUVDRJYBTL-UHFFFAOYSA-N 0.000 claims 1
- NUKFHPZNAHLRBX-UHFFFAOYSA-N 3-chloro-n-[4-(2-hydroxybutyl)-1,3-thiazol-2-yl]-5-(2-morpholin-4-ylethoxy)benzenesulfonamide Chemical compound CCC(O)CC1=CSC(NS(=O)(=O)C=2C=C(OCCN3CCOCC3)C=C(Cl)C=2)=N1 NUKFHPZNAHLRBX-UHFFFAOYSA-N 0.000 claims 1
- JFORBRUYPXLXCF-UHFFFAOYSA-N 3-chloro-n-[4-(2-hydroxypentyl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CCCC(O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 JFORBRUYPXLXCF-UHFFFAOYSA-N 0.000 claims 1
- MCPARSSNNHXFKB-UHFFFAOYSA-N 3-chloro-n-[4-(2-hydroxypropan-2-yl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(C(C)(C)O)=CS1 MCPARSSNNHXFKB-UHFFFAOYSA-N 0.000 claims 1
- BPVRNBRDKARWNN-UHFFFAOYSA-N 3-chloro-n-[4-(3-hydroxypentan-3-yl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CCC(O)(CC)C1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 BPVRNBRDKARWNN-UHFFFAOYSA-N 0.000 claims 1
- INABOHYXCCCKNV-UHFFFAOYSA-N 3-chloro-n-[4-(4-hydroxyheptan-4-yl)-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CCCC(O)(CCC)C1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 INABOHYXCCCKNV-UHFFFAOYSA-N 0.000 claims 1
- PYIMWGXAWRAJRS-UHFFFAOYSA-N 3-chloro-n-[4-[(1-hydroxycyclobutyl)methyl]-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CC2(O)CCC2)=CS1 PYIMWGXAWRAJRS-UHFFFAOYSA-N 0.000 claims 1
- ZCPDOABAPATJHC-UHFFFAOYSA-N 3-chloro-n-[4-[(1-hydroxycyclopentyl)methyl]-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CC2(O)CCCC2)=CS1 ZCPDOABAPATJHC-UHFFFAOYSA-N 0.000 claims 1
- OOZVOYCUPAZZAH-LLVKDONJSA-N 3-chloro-n-[4-[(1r)-1-hydroxypropyl]-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC[C@@H](O)C1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 OOZVOYCUPAZZAH-LLVKDONJSA-N 0.000 claims 1
- OHIWRPKTEQAIJP-UHFFFAOYSA-N 3-chloro-n-[4-[(2,3-dimethylphenyl)-hydroxymethyl]-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=CC=CC(C(O)C=2N=C(NS(=O)(=O)C=3C(=C(Cl)C=CC=3)C)SC=2)=C1C OHIWRPKTEQAIJP-UHFFFAOYSA-N 0.000 claims 1
- CGKXDSPUAANHHL-UHFFFAOYSA-N 3-chloro-n-[4-[(2,5-dimethylphenyl)-hydroxymethyl]-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=CC=C(C)C(C(O)C=2N=C(NS(=O)(=O)C=3C(=C(Cl)C=CC=3)C)SC=2)=C1 CGKXDSPUAANHHL-UHFFFAOYSA-N 0.000 claims 1
- OYSNDQGSMLGABE-UHFFFAOYSA-N 3-chloro-n-[4-[(2-cyanophenyl)-hydroxymethyl]-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(C(O)C=2C(=CC=CC=2)C#N)=CS1 OYSNDQGSMLGABE-UHFFFAOYSA-N 0.000 claims 1
- PZDRBPPYLFRQJA-UHFFFAOYSA-N 3-chloro-n-[4-[(2-ethylphenyl)-hydroxymethyl]-1,3-thiazol-2-yl]-2-methylbenzenesulfonamide Chemical compound CCC1=CC=CC=C1C(O)C1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 PZDRBPPYLFRQJA-UHFFFAOYSA-N 0.000 claims 1
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- SJTFSYATUGKODG-UHFFFAOYSA-N n-[4-[(1-hydroxycyclohexyl)methyl]-1,3-thiazol-2-yl]ethanesulfonamide Chemical compound S1C(NS(=O)(=O)CC)=NC(CC2(O)CCCCC2)=C1 SJTFSYATUGKODG-UHFFFAOYSA-N 0.000 claims 1
- NIPUSSWNTOBLKE-UHFFFAOYSA-N n-[4-[(1-hydroxycyclopentyl)methyl]-1,3-thiazol-2-yl]-2-methyl-4-(3-morpholin-4-ylpropoxy)benzenesulfonamide Chemical compound C=1C=C(S(=O)(=O)NC=2SC=C(CC3(O)CCCC3)N=2)C(C)=CC=1OCCCN1CCOCC1 NIPUSSWNTOBLKE-UHFFFAOYSA-N 0.000 claims 1
- NNCNXMPLJPXQOZ-UHFFFAOYSA-N n-[4-[(1-hydroxycyclopentyl)methyl]-1,3-thiazol-2-yl]adamantane-1-sulfonamide Chemical compound C=1SC(NS(=O)(=O)C23CC4CC(CC(C4)C2)C3)=NC=1CC1(O)CCCC1 NNCNXMPLJPXQOZ-UHFFFAOYSA-N 0.000 claims 1
- QMPLJNIYJDLHIV-UHFFFAOYSA-N n-[4-[(1-hydroxycyclopentyl)methyl]-1,3-thiazol-2-yl]cyclopropanesulfonamide Chemical compound C=1SC(NS(=O)(=O)C2CC2)=NC=1CC1(O)CCCC1 QMPLJNIYJDLHIV-UHFFFAOYSA-N 0.000 claims 1
- NDDUCXREOGHVKU-UHFFFAOYSA-N n-[4-[(1-hydroxycyclopentyl)methyl]-1,3-thiazol-2-yl]ethanesulfonamide Chemical compound S1C(NS(=O)(=O)CC)=NC(CC2(O)CCCC2)=C1 NDDUCXREOGHVKU-UHFFFAOYSA-N 0.000 claims 1
- RSTIWQDYOANAFI-UHFFFAOYSA-N n-[4-[2-(1-hydroxycyclohexyl)ethyl]-1,3-thiazol-2-yl]-2-methyl-4-(3-morpholin-4-ylpropoxy)benzenesulfonamide Chemical compound C=1C=C(S(=O)(=O)NC=2SC=C(CCC3(O)CCCCC3)N=2)C(C)=CC=1OCCCN1CCOCC1 RSTIWQDYOANAFI-UHFFFAOYSA-N 0.000 claims 1
- CBAYPBNJELWIQL-UHFFFAOYSA-N n-[4-[[4-(3-hydroxypentan-3-yl)-1,3-thiazol-2-yl]sulfamoyl]phenyl]acetamide Chemical compound CCC(O)(CC)C1=CSC(NS(=O)(=O)C=2C=CC(NC(C)=O)=CC=2)=N1 CBAYPBNJELWIQL-UHFFFAOYSA-N 0.000 claims 1
- 238000007911 parenteral administration Methods 0.000 claims 1
- 230000007170 pathology Effects 0.000 claims 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 238000007920 subcutaneous administration Methods 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 230000000699 topical effect Effects 0.000 claims 1
- 0 C[I-]1(N(*)S(c2ccccc2)(=O)=O)[N+](*)C(C*)=I(*)N1 Chemical compound C[I-]1(N(*)S(c2ccccc2)(=O)=O)[N+](*)C(C*)=I(*)N1 0.000 description 3
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
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| US63733504P | 2004-12-17 | 2004-12-17 | |
| PCT/US2005/045704 WO2006066109A2 (en) | 2004-12-17 | 2005-12-16 | Hydroxysteroid dehydrogenase inhibitors |
Publications (2)
| Publication Number | Publication Date |
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| JP2008524244A JP2008524244A (ja) | 2008-07-10 |
| JP2008524244A5 true JP2008524244A5 (enExample) | 2009-01-15 |
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| JP (1) | JP2008524244A (enExample) |
| WO (1) | WO2006066109A2 (enExample) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100222316A1 (en) | 2004-04-29 | 2010-09-02 | Abbott Laboratories | Inhibitors of the 11-beta-hydroxysteroid dehydrogenase type 1 enzyme |
| US7880001B2 (en) | 2004-04-29 | 2011-02-01 | Abbott Laboratories | Inhibitors of the 11-beta-hydroxysteroid dehydrogenase Type 1 enzyme |
| US8415354B2 (en) | 2004-04-29 | 2013-04-09 | Abbott Laboratories | Methods of use of inhibitors of the 11-beta-hydroxysteroid dehydrogenase type 1 enzyme |
| US20090192198A1 (en) | 2005-01-05 | 2009-07-30 | Abbott Laboratories | Inhibitors of the 11-beta-hydroxysteroid dehydrogenase type 1 enzyme |
| KR101496190B1 (ko) | 2005-01-05 | 2015-02-26 | 애브비 인코포레이티드 | 11-베타-하이드록시스테로이드 데하이드로게나제 타입 1 효소의 억제제로서의 아다만틸 유도체 |
| US8198331B2 (en) | 2005-01-05 | 2012-06-12 | Abbott Laboratories | Inhibitors of the 11-beta-hydroxysteroid dehydrogenase type 1 enzyme |
| CA2594116A1 (en) | 2005-01-05 | 2006-07-13 | Abbott Laboratories | Inhibitors of the 11-beta-hydroxysteroid dehydrogenase type 1 enzyme |
| CN101218235A (zh) | 2005-05-10 | 2008-07-09 | 沃泰克斯药物股份有限公司 | 作为离子通道调控剂的二环衍生物 |
| PE20080251A1 (es) | 2006-05-04 | 2008-04-25 | Boehringer Ingelheim Int | Usos de inhibidores de dpp iv |
| JP2010500300A (ja) | 2006-08-08 | 2010-01-07 | サノフィ−アベンティス | アリールアミノアリール−アルキル−置換イミダゾリジン−２，４−ジオン、それらの製造法、それらの化合物を含有する薬剤、およびそれらの使用 |
| JP5223864B2 (ja) | 2007-06-27 | 2013-06-26 | 大正製薬株式会社 | １１β−ＨＳＤ１阻害活性を有する化合物 |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| JP5736098B2 (ja) | 2007-08-21 | 2015-06-17 | アッヴィ・インコーポレイテッド | 中枢神経系障害を治療するための医薬組成物 |
| WO2010003624A2 (en) | 2008-07-09 | 2010-01-14 | Sanofi-Aventis | Heterocyclic compounds, processes for their preparation, medicaments comprising these compounds, and the use thereof |
| WO2010068601A1 (en) | 2008-12-08 | 2010-06-17 | Sanofi-Aventis | A crystalline heteroaromatic fluoroglycoside hydrate, processes for making, methods of use and pharmaceutical compositions thereof |
| SG178880A1 (en) | 2009-08-26 | 2012-04-27 | Sanofi Sa | Novel crystalline heteroaromatic fluoroglycoside hydrates, pharmaceuticals comprising these compounds and their use |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| BR112012027762B1 (pt) | 2010-04-28 | 2018-06-05 | Bayer Intellectual Property Gmbh | Derivados de cetoheteroarilpiperidina e - piperazina como fungicidas |
| EP2582709B1 (de) | 2010-06-18 | 2018-01-24 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| WO2012120054A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2683703B1 (de) | 2011-03-08 | 2015-05-27 | Sanofi | Neue substituierte phenyl-oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| WO2012120056A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Tetrasubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2012120055A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2683704B1 (de) | 2011-03-08 | 2014-12-17 | Sanofi | Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2766349B1 (de) | 2011-03-08 | 2016-06-01 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8846666B2 (en) | 2011-03-08 | 2014-09-30 | Sanofi | Oxathiazine derivatives which are substituted with benzyl or heteromethylene groups, method for producing them, their use as medicine and drug containing said derivatives and the use thereof |
| EP2683698B1 (de) | 2011-03-08 | 2017-10-04 | Sanofi | Mit adamantan- oder noradamantan substituierte benzyl-oxathiazinderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8809324B2 (en) | 2011-03-08 | 2014-08-19 | Sanofi | Substituted phenyl-oxathiazine derivatives, method for producing them, drugs containing said compounds and the use thereof |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| EP2760862B1 (en) | 2011-09-27 | 2015-10-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| TW201512171A (zh) | 2013-04-19 | 2015-04-01 | Pfizer Ltd | 化學化合物 |
| WO2017201468A1 (en) | 2016-05-20 | 2017-11-23 | Xenon Pharmaceuticals Inc. | Benzenesulfonamide compounds and their use as therapeutic agents |
| EP3551626B1 (en) * | 2016-12-09 | 2023-10-25 | Xenon Pharmaceuticals Inc. | Benzenesulfonamide compounds and their use as therapeutic agents |
| AU2019285184B2 (en) | 2018-06-13 | 2023-11-16 | Xenon Pharmaceuticals Inc. | Benzenesulfonamide compounds and their use as therapeutic agents |
| BR112021002207A2 (pt) | 2018-08-10 | 2021-05-04 | Diapin Therapeutics, Llc | tri-peptídeos e tratamento de distúrbios metabólicos, cardiovasculares e inflamatórios |
| MA53488A (fr) | 2018-08-31 | 2021-12-08 | Xenon Pharmaceuticals Inc | Composés de sulfonamide substitués par hétéroaryle et leur utilisation en tant qu'inhibiteurs de canaux sodiques |
| US10981905B2 (en) | 2018-08-31 | 2021-04-20 | Xenon Pharmaceuticals Inc. | Heteroaryl-substituted sulfonamide compounds and their use as therapeutic agents |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| SE0001899D0 (sv) * | 2000-05-22 | 2000-05-22 | Pharmacia & Upjohn Ab | New compounds |
-
2005
- 2005-12-16 WO PCT/US2005/045704 patent/WO2006066109A2/en not_active Ceased
- 2005-12-16 EP EP05854426A patent/EP1888544A2/en not_active Withdrawn
- 2005-12-16 JP JP2007546949A patent/JP2008524244A/ja not_active Withdrawn
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