JP2004532229A5 - - Google Patents
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- JP2004532229A5 JP2004532229A5 JP2002584915A JP2002584915A JP2004532229A5 JP 2004532229 A5 JP2004532229 A5 JP 2004532229A5 JP 2002584915 A JP2002584915 A JP 2002584915A JP 2002584915 A JP2002584915 A JP 2002584915A JP 2004532229 A5 JP2004532229 A5 JP 2004532229A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- imidazol
- diphenyl
- carbamic acid
- ester
- 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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- 150000001875 compounds Chemical class 0.000 claims 40
- -1 N-pyridyl Chemical group 0.000 claims 28
- 125000002947 alkylene group Chemical group 0.000 claims 27
- 125000000217 alkyl group Chemical group 0.000 claims 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 16
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims 6
- 208000002193 Pain Diseases 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- NSWZAERQBNOYAM-UHFFFAOYSA-N (2,4-difluorophenyl) n-[6-(2-methyl-4,5-diphenylimidazol-1-yl)hexyl]carbamate Chemical compound C=1C=C(F)C=C(F)C=1OC(=O)NCCCCCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 NSWZAERQBNOYAM-UHFFFAOYSA-N 0.000 claims 4
- LHAHTHILLRCRBM-UHFFFAOYSA-N (2-fluorophenyl) n-[6-(2-methyl-4,5-diphenylimidazol-1-yl)hexyl]carbamate Chemical compound C=1C=CC=C(F)C=1OC(=O)NCCCCCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 LHAHTHILLRCRBM-UHFFFAOYSA-N 0.000 claims 4
- LXGNTFODLNMYKQ-UHFFFAOYSA-N (2-fluorophenyl) n-[7-(2-methyl-4,5-diphenylimidazol-1-yl)heptan-2-yl]carbamate Chemical compound C=1C=CC=C(F)C=1OC(=O)NC(C)CCCCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 LXGNTFODLNMYKQ-UHFFFAOYSA-N 0.000 claims 4
- KVVFDLOMTIYNNM-UHFFFAOYSA-N (2-fluorophenyl) n-[7-(2-methyl-4,5-diphenylimidazol-1-yl)heptyl]carbamate Chemical compound C=1C=CC=C(F)C=1OC(=O)NCCCCCCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 KVVFDLOMTIYNNM-UHFFFAOYSA-N 0.000 claims 4
- IBVGJCKUNHQTJG-UHFFFAOYSA-N (2-methylphenyl) n-[6-(2-methyl-4,5-diphenylimidazol-1-yl)hexyl]carbamate Chemical compound C=1C=CC=C(C)C=1OC(=O)NCCCCCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 IBVGJCKUNHQTJG-UHFFFAOYSA-N 0.000 claims 4
- DNURSCPDSPXAJU-UHFFFAOYSA-N (3,4-difluorophenyl) n-[6-(2-methyl-4,5-diphenylimidazol-1-yl)hexyl]carbamate Chemical compound C=1C=C(F)C(F)=CC=1OC(=O)NCCCCCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 DNURSCPDSPXAJU-UHFFFAOYSA-N 0.000 claims 4
- XJAKUYMMKREWNM-UHFFFAOYSA-N (4-chlorophenyl) n-[6-(2-methyl-4,5-diphenylimidazol-1-yl)hexyl]carbamate Chemical compound C=1C=C(Cl)C=CC=1OC(=O)NCCCCCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 XJAKUYMMKREWNM-UHFFFAOYSA-N 0.000 claims 4
- WJLTUBGHNUKNRQ-UHFFFAOYSA-N (4-chlorophenyl) n-[7-(2-methyl-4,5-diphenylimidazol-1-yl)heptyl]carbamate Chemical compound C=1C=C(Cl)C=CC=1OC(=O)NCCCCCCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 WJLTUBGHNUKNRQ-UHFFFAOYSA-N 0.000 claims 4
- WCFPXERLDSROKC-UHFFFAOYSA-N (4-cyanophenyl) n-[7-(2-methyl-4,5-diphenylimidazol-1-yl)heptyl]carbamate Chemical compound C=1C=C(C#N)C=CC=1OC(=O)NCCCCCCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 WCFPXERLDSROKC-UHFFFAOYSA-N 0.000 claims 4
- CSFBUGVVQNTZGS-UHFFFAOYSA-N (4-fluorophenyl) n-[6-(2-methyl-4,5-diphenylimidazol-1-yl)hexyl]carbamate Chemical compound C=1C=C(F)C=CC=1OC(=O)NCCCCCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 CSFBUGVVQNTZGS-UHFFFAOYSA-N 0.000 claims 4
- UWKODOYNVJUKMA-UHFFFAOYSA-N phenyl n-[7-(2-methyl-4,5-diphenylimidazol-1-yl)heptyl]carbamate Chemical compound C=1C=CC=CC=1OC(=O)NCCCCCCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 UWKODOYNVJUKMA-UHFFFAOYSA-N 0.000 claims 4
- QMIKRYNXYTZTKA-UHFFFAOYSA-N (2,4-difluorophenyl) n-[5-(2-methyl-4,5-diphenylimidazol-1-yl)pentyl]carbamate Chemical compound C=1C=C(F)C=C(F)C=1OC(=O)NCCCCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 QMIKRYNXYTZTKA-UHFFFAOYSA-N 0.000 claims 3
- ZFCUKLAHWGJHDA-UHFFFAOYSA-N (2,4-difluorophenyl) n-[7-(2-methyl-4,5-diphenylimidazol-1-yl)heptyl]carbamate Chemical compound C=1C=C(F)C=C(F)C=1OC(=O)NCCCCCCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 ZFCUKLAHWGJHDA-UHFFFAOYSA-N 0.000 claims 3
- FTFMPYWXZDLNAM-UHFFFAOYSA-N (2,6-difluorophenyl) n-[6-[4,5-bis(4-fluorophenyl)-2-methylimidazol-1-yl]hexyl]carbamate Chemical compound FC=1C=CC=C(F)C=1OC(=O)NCCCCCCN1C(C)=NC(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 FTFMPYWXZDLNAM-UHFFFAOYSA-N 0.000 claims 3
- BWPRPBUIQPVVFD-UHFFFAOYSA-N (2-fluorophenyl) n-[5-(2-methyl-4,5-diphenylimidazol-1-yl)pentyl]carbamate Chemical compound C=1C=CC=C(F)C=1OC(=O)NCCCCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 BWPRPBUIQPVVFD-UHFFFAOYSA-N 0.000 claims 3
- FROPPAHABGJTLA-UHFFFAOYSA-N (2-fluorophenyl) n-[6-[4,5-bis(4-fluorophenyl)-2-methylimidazol-1-yl]hexyl]carbamate Chemical compound C=1C=CC=C(F)C=1OC(=O)NCCCCCCN1C(C)=NC(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 FROPPAHABGJTLA-UHFFFAOYSA-N 0.000 claims 3
- IUNZJOWJONPLGO-UHFFFAOYSA-N (2-methoxyphenyl) n-[7-(2-methyl-4,5-diphenylimidazol-1-yl)heptyl]carbamate Chemical compound COC1=CC=CC=C1OC(=O)NCCCCCCCN1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N=C1C IUNZJOWJONPLGO-UHFFFAOYSA-N 0.000 claims 3
- NBASSYYNACEAGJ-UHFFFAOYSA-N (2-methylphenyl) n-[7-(2-methyl-4,5-diphenylimidazol-1-yl)heptyl]carbamate Chemical compound C=1C=CC=C(C)C=1OC(=O)NCCCCCCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 NBASSYYNACEAGJ-UHFFFAOYSA-N 0.000 claims 3
- UGSXGFMGLUGUAU-UHFFFAOYSA-N (4-chlorophenyl) n-[5-(2-methyl-4,5-diphenylimidazol-1-yl)pentyl]carbamate Chemical compound C=1C=C(Cl)C=CC=1OC(=O)NCCCCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 UGSXGFMGLUGUAU-UHFFFAOYSA-N 0.000 claims 3
- JQCVZSZSAVHKDK-UHFFFAOYSA-N (4-cyanophenyl) n-[5-(2-methyl-4,5-diphenylimidazol-1-yl)pentyl]carbamate Chemical compound C=1C=C(C#N)C=CC=1OC(=O)NCCCCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 JQCVZSZSAVHKDK-UHFFFAOYSA-N 0.000 claims 3
- LNRLTYJRJMLPES-UHFFFAOYSA-N (4-cyanophenyl) n-[6-(2-methyl-4,5-diphenylimidazol-1-yl)hexyl]carbamate Chemical compound C=1C=C(C#N)C=CC=1OC(=O)NCCCCCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 LNRLTYJRJMLPES-UHFFFAOYSA-N 0.000 claims 3
- LJVAEURIXMPCHM-UHFFFAOYSA-N (4-fluorophenyl) n-[5-(2-methyl-4,5-diphenylimidazol-1-yl)pentyl]carbamate Chemical compound C=1C=C(F)C=CC=1OC(=O)NCCCCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 LJVAEURIXMPCHM-UHFFFAOYSA-N 0.000 claims 3
- YEYYSMBWLXKXSJ-UHFFFAOYSA-N (4-fluorophenyl) n-[7-(2-methyl-4,5-diphenylimidazol-1-yl)heptyl]carbamate Chemical compound C=1C=C(F)C=CC=1OC(=O)NCCCCCCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 YEYYSMBWLXKXSJ-UHFFFAOYSA-N 0.000 claims 3
- ZCXQKBFXBDHCMV-UHFFFAOYSA-N (4-methoxyphenyl) n-[5-(2-methyl-4,5-diphenylimidazol-1-yl)pentyl]carbamate Chemical compound C1=CC(OC)=CC=C1OC(=O)NCCCCCN1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N=C1C ZCXQKBFXBDHCMV-UHFFFAOYSA-N 0.000 claims 3
- ABKJPGCDYPXWKQ-UHFFFAOYSA-N (4-methoxyphenyl) n-[6-(2-methyl-4,5-diphenylimidazol-1-yl)hexyl]carbamate Chemical compound C1=CC(OC)=CC=C1OC(=O)NCCCCCCN1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N=C1C ABKJPGCDYPXWKQ-UHFFFAOYSA-N 0.000 claims 3
- VLPBIVLQDLAAMM-UHFFFAOYSA-N (4-methoxyphenyl) n-[7-(2-methyl-4,5-diphenylimidazol-1-yl)heptyl]carbamate Chemical compound C1=CC(OC)=CC=C1OC(=O)NCCCCCCCN1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N=C1C VLPBIVLQDLAAMM-UHFFFAOYSA-N 0.000 claims 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 3
- CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 claims 3
- ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 claims 3
- UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 claims 3
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
- VJHMAYPKFOEEMF-UHFFFAOYSA-N ethyl n-[7-(2-methyl-4,5-diphenylimidazol-1-yl)heptyl]carbamate Chemical compound CCOC(=O)NCCCCCCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 VJHMAYPKFOEEMF-UHFFFAOYSA-N 0.000 claims 3
- 208000004296 neuralgia Diseases 0.000 claims 3
- 208000021722 neuropathic pain Diseases 0.000 claims 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims 3
- VNIZFYRBACXAQP-UHFFFAOYSA-N phenyl n-[5-(2-methyl-4,5-diphenylimidazol-1-yl)pentyl]carbamate Chemical compound C=1C=CC=CC=1OC(=O)NCCCCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 VNIZFYRBACXAQP-UHFFFAOYSA-N 0.000 claims 3
- KCHOVCICRIAYSX-UHFFFAOYSA-N phenyl n-[6-(2-methyl-4,5-diphenylimidazol-1-yl)hexyl]carbamate Chemical compound C=1C=CC=CC=1OC(=O)NCCCCCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 KCHOVCICRIAYSX-UHFFFAOYSA-N 0.000 claims 3
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- AYBJAAXONTZTRT-UHFFFAOYSA-N (2,6-dimethoxyphenyl) n-[5-(2-methyl-4,5-diphenylimidazol-1-yl)pentyl]carbamate Chemical compound COC1=CC=CC(OC)=C1OC(=O)NCCCCCN1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N=C1C AYBJAAXONTZTRT-UHFFFAOYSA-N 0.000 claims 2
- TXTYAAMKKBDEHL-UHFFFAOYSA-N (2,6-dimethoxyphenyl) n-[6-(2-methyl-4,5-diphenylimidazol-1-yl)hexyl]carbamate Chemical compound COC1=CC=CC(OC)=C1OC(=O)NCCCCCCN1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N=C1C TXTYAAMKKBDEHL-UHFFFAOYSA-N 0.000 claims 2
- VHHYCPSXRJPUPU-UHFFFAOYSA-N (2,6-dimethoxyphenyl) n-[7-(2-methyl-4,5-diphenylimidazol-1-yl)heptyl]carbamate Chemical compound COC1=CC=CC(OC)=C1OC(=O)NCCCCCCCN1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N=C1C VHHYCPSXRJPUPU-UHFFFAOYSA-N 0.000 claims 2
- HMJCRVRGZFQOMD-UHFFFAOYSA-N (2-fluorophenyl) n-[2-methyl-8-(2-methyl-4,5-diphenylimidazol-1-yl)octan-3-yl]carbamate Chemical compound C=1C=CC=C(F)C=1OC(=O)NC(C(C)C)CCCCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 HMJCRVRGZFQOMD-UHFFFAOYSA-N 0.000 claims 2
- LVGPJSBRMDHIRR-UHFFFAOYSA-N (2-fluorophenyl) n-[6-(2-methyl-4,5-diphenylimidazol-1-yl)-1-phenylhexyl]carbamate Chemical compound C=1C=CC=C(F)C=1OC(=O)NC(C=1C=CC=CC=1)CCCCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 LVGPJSBRMDHIRR-UHFFFAOYSA-N 0.000 claims 2
- BDZLAFXHYNNBSK-UHFFFAOYSA-N (2-fluorophenyl) n-[8-(2-methyl-4,5-diphenylimidazol-1-yl)octan-3-yl]carbamate Chemical compound C=1C=CC=C(F)C=1OC(=O)NC(CC)CCCCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 BDZLAFXHYNNBSK-UHFFFAOYSA-N 0.000 claims 2
- WUTDHSLCSCRJJE-UHFFFAOYSA-N (2-methoxyphenyl) n-[4-[3-(2-methyl-4,5-diphenylimidazol-1-yl)propoxy]phenyl]carbamate Chemical compound COC1=CC=CC=C1OC(=O)NC(C=C1)=CC=C1OCCCN1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N=C1C WUTDHSLCSCRJJE-UHFFFAOYSA-N 0.000 claims 2
- FZGDFPYGTTVJHF-UHFFFAOYSA-N (2-methoxyphenyl) n-[5-(2-methyl-4,5-diphenylimidazol-1-yl)pentyl]carbamate Chemical compound COC1=CC=CC=C1OC(=O)NCCCCCN1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N=C1C FZGDFPYGTTVJHF-UHFFFAOYSA-N 0.000 claims 2
- SDPQMYWYNNWTLU-UHFFFAOYSA-N (2-methoxyphenyl) n-[6-(2-methyl-4,5-diphenylimidazol-1-yl)hexyl]carbamate Chemical compound COC1=CC=CC=C1OC(=O)NCCCCCCN1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N=C1C SDPQMYWYNNWTLU-UHFFFAOYSA-N 0.000 claims 2
- UXFHDVNGNFTBIX-UHFFFAOYSA-N (2-methylphenyl) n-[5-(2-methyl-4,5-diphenylimidazol-1-yl)pentyl]carbamate Chemical compound C=1C=CC=C(C)C=1OC(=O)NCCCCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 UXFHDVNGNFTBIX-UHFFFAOYSA-N 0.000 claims 2
- RFLKXRLXXACOCO-UHFFFAOYSA-N (3-chlorophenyl) n-[4-[3-(2-methyl-4,5-diphenylimidazol-1-yl)propoxy]phenyl]carbamate Chemical compound C=1C=C(NC(=O)OC=2C=C(Cl)C=CC=2)C=CC=1OCCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 RFLKXRLXXACOCO-UHFFFAOYSA-N 0.000 claims 2
- QLVDMDDQLWVPLM-UHFFFAOYSA-N (4-chlorophenyl) n-[4-[3-(2-methyl-4,5-diphenylimidazol-1-yl)propoxy]phenyl]carbamate Chemical compound C=1C=C(NC(=O)OC=2C=CC(Cl)=CC=2)C=CC=1OCCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 QLVDMDDQLWVPLM-UHFFFAOYSA-N 0.000 claims 2
- CTCPSLZBROEIJK-UHFFFAOYSA-N (4-methoxyphenyl) n-[4-[3-(2-methyl-4,5-diphenylimidazol-1-yl)propoxy]phenyl]carbamate Chemical compound C1=CC(OC)=CC=C1OC(=O)NC(C=C1)=CC=C1OCCCN1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N=C1C CTCPSLZBROEIJK-UHFFFAOYSA-N 0.000 claims 2
- 208000000094 Chronic Pain Diseases 0.000 claims 2
- 208000005298 acute pain Diseases 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- VZSXUVQCPYUMAW-UHFFFAOYSA-N ethyl n-[5-(2-methyl-4,5-diphenylimidazol-1-yl)pentyl]carbamate Chemical compound CCOC(=O)NCCCCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 VZSXUVQCPYUMAW-UHFFFAOYSA-N 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- CRYHRFPPPYGXLU-UHFFFAOYSA-N methyl n-[6-(2-methyl-4,5-diphenylimidazol-1-yl)hexyl]carbamate Chemical compound COC(=O)NCCCCCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 CRYHRFPPPYGXLU-UHFFFAOYSA-N 0.000 claims 2
- OFSWZLPOOKDXDP-UHFFFAOYSA-N methyl n-[7-(2-methyl-4,5-diphenylimidazol-1-yl)heptyl]carbamate Chemical compound COC(=O)NCCCCCCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 OFSWZLPOOKDXDP-UHFFFAOYSA-N 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- HVBXMFCCTUBMJH-UHFFFAOYSA-N (2-fluorophenyl) n-[4-[2-(2-methyl-4,5-diphenylimidazol-1-yl)ethoxy]phenyl]carbamate Chemical compound C=1C=C(NC(=O)OC=2C(=CC=CC=2)F)C=CC=1OCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 HVBXMFCCTUBMJH-UHFFFAOYSA-N 0.000 claims 1
- RUFUOXCZFVHSGF-UHFFFAOYSA-N (2-fluorophenyl) n-[4-[3-(2-methyl-4,5-diphenylimidazol-1-yl)propoxy]phenyl]carbamate Chemical compound C=1C=C(NC(=O)OC=2C(=CC=CC=2)F)C=CC=1OCCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 RUFUOXCZFVHSGF-UHFFFAOYSA-N 0.000 claims 1
- IDONYIIJPCLJKI-UHFFFAOYSA-N (3,4-difluorophenyl) n-[4-[2-(2-methyl-4,5-diphenylimidazol-1-yl)ethoxy]phenyl]carbamate Chemical compound C=1C=C(NC(=O)OC=2C=C(F)C(F)=CC=2)C=CC=1OCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 IDONYIIJPCLJKI-UHFFFAOYSA-N 0.000 claims 1
- CYCGLDOPUFZCSV-UHFFFAOYSA-N (3,4-difluorophenyl) n-[4-[3-(2-methyl-4,5-diphenylimidazol-1-yl)propoxy]phenyl]carbamate Chemical compound C=1C=C(NC(=O)OC=2C=C(F)C(F)=CC=2)C=CC=1OCCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 CYCGLDOPUFZCSV-UHFFFAOYSA-N 0.000 claims 1
- WOLFTIJTUYIRFQ-UHFFFAOYSA-N (4-chlorophenyl) n-[4-[2-(2-methyl-4,5-diphenylimidazol-1-yl)ethoxy]phenyl]carbamate Chemical compound C=1C=C(NC(=O)OC=2C=CC(Cl)=CC=2)C=CC=1OCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 WOLFTIJTUYIRFQ-UHFFFAOYSA-N 0.000 claims 1
- SHTWNZPEBIGSSW-UHFFFAOYSA-N (4-fluorophenyl) n-[4-[2-(2-methyl-4,5-diphenylimidazol-1-yl)ethoxy]phenyl]carbamate Chemical compound C=1C=C(NC(=O)OC=2C=CC(F)=CC=2)C=CC=1OCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 SHTWNZPEBIGSSW-UHFFFAOYSA-N 0.000 claims 1
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 206010001513 AIDS related complex Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 208000030814 Eating disease Diseases 0.000 claims 1
- 102100027297 Fatty acid 2-hydroxylase Human genes 0.000 claims 1
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 101000937693 Homo sapiens Fatty acid 2-hydroxylase Proteins 0.000 claims 1
- 101000918494 Homo sapiens Fatty-acid amide hydrolase 1 Proteins 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
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- NGMMWUXERKZVJI-UHFFFAOYSA-N butan-2-yl n-[6-(2-ethyl-4,5-diphenylimidazol-1-yl)hexyl]carbamate Chemical compound CCC(C)OC(=O)NCCCCCCN1C(CC)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 NGMMWUXERKZVJI-UHFFFAOYSA-N 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- JCUFQSXXINWVIU-UHFFFAOYSA-N cyclohexyl n-[6-(2-methyl-4,5-diphenylimidazol-1-yl)hexyl]carbamate Chemical compound C1CCCCC1OC(=O)NCCCCCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 JCUFQSXXINWVIU-UHFFFAOYSA-N 0.000 claims 1
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- WIHGSFJBAYXSNS-UHFFFAOYSA-N ethyl n-[4-[2-(2-methyl-4,5-diphenylimidazol-1-yl)ethoxy]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1OCCN1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N=C1C WIHGSFJBAYXSNS-UHFFFAOYSA-N 0.000 claims 1
- GSVJWQNGCOHAMM-UHFFFAOYSA-N ethyl n-[6-(2-methyl-4,5-diphenylimidazol-1-yl)hexyl]carbamate Chemical compound CCOC(=O)NCCCCCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 GSVJWQNGCOHAMM-UHFFFAOYSA-N 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
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- RNYLSGGTAIRFDR-UHFFFAOYSA-N phenyl n-[4-[2-(2-methyl-4,5-diphenylimidazol-1-yl)ethoxy]phenyl]carbamate Chemical compound C=1C=C(NC(=O)OC=2C=CC=CC=2)C=CC=1OCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 RNYLSGGTAIRFDR-UHFFFAOYSA-N 0.000 claims 1
- JKCXQDIHXXYILY-UHFFFAOYSA-N phenyl n-[4-[3-(2-methyl-4,5-diphenylimidazol-1-yl)propoxy]phenyl]carbamate Chemical compound C=1C=C(NC(=O)OC=2C=CC=CC=2)C=CC=1OCCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 JKCXQDIHXXYILY-UHFFFAOYSA-N 0.000 claims 1
- DWNVRDYRAQCINB-UHFFFAOYSA-N propan-2-yl n-[6-(2-methyl-4,5-diphenylimidazol-1-yl)hexyl]carbamate Chemical compound CC(C)OC(=O)NCCCCCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 DWNVRDYRAQCINB-UHFFFAOYSA-N 0.000 claims 1
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- VLTNNAFYFSVVGS-UHFFFAOYSA-N tert-butyl n-[6-(2-ethyl-4,5-diphenylimidazol-1-yl)hexyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCCCCN1C(CC)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 VLTNNAFYFSVVGS-UHFFFAOYSA-N 0.000 claims 1
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| CA2442330A1 (en) * | 2001-03-29 | 2002-10-10 | Emory University | Acute pharmacologic augmentation of psychotherapy with enhancers of learning or conditioning |
| US6949574B2 (en) * | 2002-02-08 | 2005-09-27 | Bristol-Myers Squibb Company | (Oxime)carbamoyl fatty acid amide hydrolase inhibitors |
| EA010267B1 (ru) | 2002-10-07 | 2008-06-30 | Те Риджентс Оф Те Юниверсити Оф Калифорния | Модуляция тревоги через блокаду гидролиза анандамида |
| FR2850377B1 (fr) * | 2003-01-23 | 2009-02-20 | Sanofi Synthelabo | Derives d'arylalkylcarbamates, leur preparation et leur application en therapeutique |
| FR2865205B1 (fr) | 2004-01-16 | 2006-02-24 | Sanofi Synthelabo | Derives de type aryloxyalkylcarbamates, leur preparation et leur application en therapeutique |
| FR2866886B1 (fr) * | 2004-02-26 | 2007-08-31 | Sanofi Synthelabo | Derives d'aryl-et d'heteroaryl-akylcarbamates, leur preparation et leur application en therapeutique |
| FR2866884B1 (fr) * | 2004-02-26 | 2007-08-31 | Sanofi Synthelabo | Derives d'aryl-et d'heteroaryl-piperidinecarboxylates, leur preparation et leur application en therapeutique |
| FR2866885B1 (fr) | 2004-02-26 | 2007-08-31 | Sanofi Synthelabo | Derives de piperidinylalkylcarbamates, leur prepation et leur application en therapeutique |
| EP1742626A2 (en) * | 2004-04-23 | 2007-01-17 | The Regents of The University of California | Compounds and methods for treating non-inflammatory pain using pparalpha agonists |
| WO2006044617A1 (en) | 2004-10-15 | 2006-04-27 | The Scripps Research Institute | Oxadiazole ketone inhibitors of fatty acid amide hydrolase |
| US20060084659A1 (en) * | 2004-10-19 | 2006-04-20 | Michael Davis | Augmentation of psychotherapy with cannabinoid reuptake inhibitors |
| TW200633990A (en) | 2004-11-18 | 2006-10-01 | Takeda Pharmaceuticals Co | Amide compound |
| NZ590148A (en) | 2004-12-30 | 2012-04-27 | Janssen Pharmaceutica Nv | Piperazinyl and piperidinyl ureas as modulators of fatty acid amide hydrolase |
| ZA200709038B (en) * | 2005-04-13 | 2009-01-28 | Neuraxon Inc | Substituted indole compounds having nos inhibitory activity |
| WO2006116773A2 (en) * | 2005-04-28 | 2006-11-02 | The Regents Of The University Of California | Methods, compositions, and compounds for modulation of monoacylglycerol lipase, pain, and stress-related disorders |
| EP1983994B1 (en) | 2006-02-17 | 2015-09-30 | The Scripps Research Institute | Oxazole ketones as modulators of fatty acid amide hydrolase |
| KR100753240B1 (ko) | 2006-03-10 | 2007-08-30 | 한국지질자원연구원 | 합금 나노분말의 제조방법 |
| CA2702468A1 (en) | 2007-10-12 | 2009-04-23 | University Of Connecticut | Therapeutic applications of fatty acid amide hydrolase inhibitors |
| EP2062578A1 (en) * | 2007-11-12 | 2009-05-27 | Institut National De La Sante Et De La Recherche Medicale (Inserm) | Novel use of chemical compounds for the treatment of AIDS |
| EA201000808A1 (ru) | 2007-11-16 | 2011-04-29 | Ньюраксон, Инк. | Индольные соединения и способы лечения висцеральной боли |
| EP2254415B1 (en) | 2008-02-19 | 2013-01-23 | Janssen Pharmaceutica, N.V. | Aryl-hydroxyethylamino-pyrimidines and triazines as modulators of fatty acid amide hydrolase |
| US8207226B1 (en) | 2008-06-03 | 2012-06-26 | Alcon Research, Ltd. | Use of FAAH antagonists for treating dry eye and ocular pain |
| WO2010068452A1 (en) | 2008-11-25 | 2010-06-17 | Janssen Pharmaceutica Nv | Heteroaryl-substituted urea modulators of fatty acid amide hydrolase |
| US8461159B2 (en) | 2008-11-25 | 2013-06-11 | Jannsen Pharmaceutica BV | Heteroaryl-substituted urea modulators of fatty acid amide hydrolase |
| US20120083476A1 (en) | 2009-06-05 | 2012-04-05 | Janssen Pharmaceutica Nv | Heteroaryl-substituted spirocyclic diamine urea modulators of fatty acid amide hydrolase |
| US8901111B2 (en) | 2009-06-05 | 2014-12-02 | Janssen Pharmaceutica Nv | Aryl-substituted heterocyclic urea modulators of fatty acid amide hydrolase |
| US8906914B2 (en) | 2009-08-18 | 2014-12-09 | Janssen Pharmaceutica Nv | Ethylene diamine modulators of fatty acid hydrolase |
| US8735406B2 (en) | 2009-09-09 | 2014-05-27 | Dainippon Sumitomo Pharma Co., Ltd. | 8-oxodihydropurine derivative |
| US20120225097A1 (en) | 2009-11-12 | 2012-09-06 | Hawryluk Natalie A | Piperazinecarboxamide derivative useful as a modulator of fatty acid amide hydrolase (faah) |
| UA108233C2 (uk) | 2010-05-03 | 2015-04-10 | Модулятори активності гідролази амідів жирних кислот | |
| DE102012018115A1 (de) | 2012-09-13 | 2014-03-13 | Matthias Lehr | Aryl-N-(arylalkyl)carbamate als Hemmstoffe der Fatty Acid Amide Hydrolase |
| EP2931291B1 (en) | 2012-12-11 | 2021-10-20 | The McLean Hospital Corporation | Xenon treatment as an adjunct to psychotherapy for psychiatric disorders |
| DE102013016573A1 (de) | 2013-10-04 | 2015-04-09 | Matthias Lehr | 1-Tetrazolylpropan-2-one als Inhibitoren von cytosolischer Phospholipase A2 und Fatty Acid Amide Hydrolase, insbesondere geeignet zur topischen Anwendung |
| US10414721B1 (en) | 2018-06-04 | 2019-09-17 | University Of Bern | Inhibitor of endocannabinoid cellular reuptake |
| CN111269083B (zh) * | 2020-02-24 | 2023-08-25 | 珠海市柏瑞医药科技有限公司 | 一种格尔伯特酸的合成方法 |
| US11999703B1 (en) | 2023-10-25 | 2024-06-04 | King Faisal University | 5-(2,4,5-tris(4-chlorophenyl)-1H-imidazol-1-yl)pentanoic acid as an antimicrobial compound |
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| NO893909L (no) * | 1988-10-03 | 1990-04-04 | Glaxo Group Ltd | Fremgangsmaate for fremstilling av terapeutisk aktive imidazol-derivater. |
| ATE193290T1 (de) * | 1992-02-11 | 2000-06-15 | Smithkline Beecham Corp | Coa-it- und paf-inhibitoren |
| US5700826A (en) * | 1995-06-07 | 1997-12-23 | Ontogen Corporation | 1,2,4,5-tetra substituted imidazoles as modulators of multi-drug resistance |
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2002
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- 2002-04-23 EP EP02728952A patent/EP1389107A4/en not_active Withdrawn
- 2002-04-23 MX MXPA03009850A patent/MXPA03009850A/es active IP Right Grant
- 2002-04-23 CA CA002445294A patent/CA2445294A1/en not_active Abandoned
- 2002-04-23 IL IL15830002A patent/IL158300A0/xx unknown
- 2002-04-23 WO PCT/US2002/012853 patent/WO2002087569A1/en not_active Ceased
- 2002-04-23 JP JP2002584915A patent/JP2004532229A/ja active Pending
-
2004
- 2004-07-01 US US10/883,195 patent/USRE39634E1/en not_active Expired - Lifetime