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 |
|---|---|---|---|
| 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 |
|---|---|
| JP2008524244A JP2008524244A (ja) | 2008-07-10 |
| JP2008524244A5 true JP2008524244A5 (enExample) | 2009-01-15 |
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| JP2007546949A Withdrawn JP2008524244A (ja) | 2004-12-17 | 2005-12-16 | 水酸化ステロイド脱水素酵素阻害剤 |
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| EP (1) | EP1888544A2 (enExample) |
| JP (1) | JP2008524244A (enExample) |
| WO (1) | WO2006066109A2 (enExample) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US20100222316A1 (en) | 2004-04-29 | 2010-09-02 | Abbott Laboratories | 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 |
| US7511175B2 (en) | 2005-01-05 | 2009-03-31 | Abbott Laboratories | Inhibitors of the 11-beta-hydroxysteroid dehydrogenase type 1 enzyme |
| US7217838B2 (en) | 2005-01-05 | 2007-05-15 | Abbott Laboratories | Inhibitors of the 11-beta-hydroxysteroid dehydrogenase type 1 enzyme |
| US8198331B2 (en) | 2005-01-05 | 2012-06-12 | Abbott Laboratories | Inhibitors of the 11-beta-hydroxysteroid dehydrogenase type 1 enzyme |
| RU2007145434A (ru) * | 2005-05-10 | 2009-06-20 | Вертекс Фармасьютикалз Инкорпорейтед (Us) | Бициклические производные в качестве модуляторов ионных каналов |
| PE20080251A1 (es) | 2006-05-04 | 2008-04-25 | Boehringer Ingelheim Int | Usos de inhibidores de dpp iv |
| EP2061767B1 (de) | 2006-08-08 | 2014-12-17 | Sanofi | Arylaminoaryl-alkyl-substituierte Imidazolidin-2,4-dione, Verfahren zu ihrer Herstellung, diese Verbindungen enthaltende Arzneimittel und ihre Verwendung |
| EP2172453A4 (en) | 2007-06-27 | 2010-12-22 | Taisho Pharmaceutical Co Ltd | CONNECTION WITH 11-β-HSD1 INHIBITING ACTIVITY |
| 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 |
| US8470841B2 (en) | 2008-07-09 | 2013-06-25 | Sanofi | 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 |
| CN102482312A (zh) | 2009-08-26 | 2012-05-30 | 赛诺菲 | 新颖的杂芳族氟代糖苷结晶水合物、含有这些化合物的药物和它们的用途 |
| 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 |
| WO2012120053A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2683702B1 (de) | 2011-03-08 | 2014-12-24 | Sanofi | Neue substituierte phenyl-oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8901114B2 (en) | 2011-03-08 | 2014-12-02 | Sanofi | Oxathiazine derivatives substituted with carbocycles or heterocycles, method for producing same, drugs containing said compounds, and use thereof |
| WO2012120051A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Mit adamantan- oder noradamantan substituierte benzyl-oxathiazinderivate, 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 |
| 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 |
| EP2683703B1 (de) | 2011-03-08 | 2015-05-27 | Sanofi | Neue substituierte phenyl-oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2683705B1 (de) | 2011-03-08 | 2015-04-22 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2683699B1 (de) | 2011-03-08 | 2015-06-24 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| 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 |
| HUE071358T2 (hu) | 2016-05-20 | 2025-08-28 | Xenon Pharmaceuticals Inc | Benzolszulfonamid vegyületek és terápiás szerként való alkalmazásuk |
| JP7022751B2 (ja) * | 2016-12-09 | 2022-02-18 | ゼノン・ファーマシューティカルズ・インコーポレイテッド | ベンゼンスルホンアミド化合物および治療剤としてのそれらの使用 |
| SG11202011862PA (en) | 2018-06-13 | 2020-12-30 | Xenon Pharmaceuticals Inc | Benzenesulfonamide compounds and their use as therapeutic agents |
| MX2021001380A (es) | 2018-08-31 | 2021-05-27 | Xenon Pharmaceuticals Inc | Compuestos de sulfonamida sustituidos con heteroarilo y su uso como agentes terapeuticos. |
| CN112638898B (zh) | 2018-08-31 | 2024-04-09 | 泽农医药公司 | 杂芳基取代的磺酰胺化合物及其作为钠通道抑制剂的用途 |
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 JP JP2007546949A patent/JP2008524244A/ja not_active Withdrawn
- 2005-12-16 EP EP05854426A patent/EP1888544A2/en not_active Withdrawn
- 2005-12-16 WO PCT/US2005/045704 patent/WO2006066109A2/en not_active Ceased
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