JP2015531746A5 - - Google Patents
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- Publication number
- JP2015531746A5 JP2015531746A5 JP2015517189A JP2015517189A JP2015531746A5 JP 2015531746 A5 JP2015531746 A5 JP 2015531746A5 JP 2015517189 A JP2015517189 A JP 2015517189A JP 2015517189 A JP2015517189 A JP 2015517189A JP 2015531746 A5 JP2015531746 A5 JP 2015531746A5
- Authority
- JP
- Japan
- Prior art keywords
- methylsulfamate
- dioxolan
- dioxaspiro
- dimethyl
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 23
- 150000003839 salts Chemical class 0.000 claims 11
- 239000000126 substance Substances 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 3
- 208000007101 Muscle Cramp Diseases 0.000 claims 3
- 208000005392 Spasm Diseases 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- BPXFHCPFOMZFSW-UHFFFAOYSA-N (2-phenyl-1,4-dioxaspiro[4.5]decan-3-yl) n-methylsulfamate Chemical compound O1C(C=2C=CC=CC=2)C(OS(=O)(=O)NC)OC21CCCCC2 BPXFHCPFOMZFSW-UHFFFAOYSA-N 0.000 claims 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 2
- -1 5- (2-Methylphenyl) -2,2-diethyl-1,3-dioxolan-4-yl Chemical group 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- NLNWCJGUMAOWED-UHFFFAOYSA-N [2,2-dimethyl-5-(2-methylphenyl)-1,3-dioxolan-4-yl] n-methylsulfamate Chemical compound CNS(=O)(=O)OC1OC(C)(C)OC1C1=CC=CC=C1C NLNWCJGUMAOWED-UHFFFAOYSA-N 0.000 claims 2
- GAFWODMWEDQVPY-UHFFFAOYSA-N [2-(2-chlorophenyl)-1,4-dioxaspiro[4.5]decan-3-yl] n-methylsulfamate Chemical compound O1C(C=2C(=CC=CC=2)Cl)C(OS(=O)(=O)NC)OC21CCCCC2 GAFWODMWEDQVPY-UHFFFAOYSA-N 0.000 claims 2
- QWOWRIOCXVQFRR-UHFFFAOYSA-N [5-(2,6-dichlorophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound O1C(C)(C)OC(COS(N)(=O)=O)C1C1=C(Cl)C=CC=C1Cl QWOWRIOCXVQFRR-UHFFFAOYSA-N 0.000 claims 2
- XHAGRJPHZXUFFK-UHFFFAOYSA-N [5-(2-chlorophenyl)-2,2-diethyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound O1C(CC)(CC)OC(COS(N)(=O)=O)C1C1=CC=CC=C1Cl XHAGRJPHZXUFFK-UHFFFAOYSA-N 0.000 claims 2
- RZMCTLKVIWUBPA-UHFFFAOYSA-N [5-(2-chlorophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound O1C(C)(C)OC(COS(N)(=O)=O)C1C1=CC=CC=C1Cl RZMCTLKVIWUBPA-UHFFFAOYSA-N 0.000 claims 2
- ZJTMPSSKRYNKNG-UHFFFAOYSA-N [5-(2-chlorophenyl)-2-methyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound S(N)(OCC1OC(OC1C1=C(C=CC=C1)Cl)C)(=O)=O ZJTMPSSKRYNKNG-UHFFFAOYSA-N 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 230000003287 optical effect Effects 0.000 claims 2
- LMQRBDRDPMHJMX-UHFFFAOYSA-N (2,2-diethyl-5-phenyl-1,3-dioxolan-4-yl) n-methylsulfamate Chemical compound O1C(CC)(CC)OC(OS(=O)(=O)NC)C1C1=CC=CC=C1 LMQRBDRDPMHJMX-UHFFFAOYSA-N 0.000 claims 1
- ARXALQHZXOMTOE-UHFFFAOYSA-N (2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl) n-methylsulfamate Chemical compound CNS(=O)(=O)OC1OC(C)(C)OC1C1=CC=CC=C1 ARXALQHZXOMTOE-UHFFFAOYSA-N 0.000 claims 1
- XMZAUZFKKTXOSV-UHFFFAOYSA-N (2-benzyl-1,4-dioxaspiro[4.4]nonan-3-yl) N-methylsulfamate Chemical compound CNS(OC1OC2(OC1CC1=CC=CC=C1)CCCC2)(=O)=O XMZAUZFKKTXOSV-UHFFFAOYSA-N 0.000 claims 1
- WNYSYNQULPQYPN-UHFFFAOYSA-N (2-benzyl-1,4-dioxaspiro[4.5]decan-3-yl) N-methylsulfamate Chemical compound CNS(OC1OC2(OC1CC1=CC=CC=C1)CCCCC2)(=O)=O WNYSYNQULPQYPN-UHFFFAOYSA-N 0.000 claims 1
- HWPQDDRMEZFVAT-UHFFFAOYSA-N (2-phenyl-1,4-dioxaspiro[4.4]nonan-3-yl) n-methylsulfamate Chemical compound O1C(C=2C=CC=CC=2)C(OS(=O)(=O)NC)OC21CCCC2 HWPQDDRMEZFVAT-UHFFFAOYSA-N 0.000 claims 1
- KSMPNKLYNWJXNI-UHFFFAOYSA-N (5-benzyl-2,2-diethyl-1,3-dioxolan-4-yl)methyl sulfamate Chemical compound S(N)(OCC1OC(OC1CC1=CC=CC=C1)(CC)CC)(=O)=O KSMPNKLYNWJXNI-UHFFFAOYSA-N 0.000 claims 1
- GPQXADGDQZYFMV-UHFFFAOYSA-N (5-benzyl-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfamate Chemical compound S(N)(OCC1OC(OC1CC1=CC=CC=C1)(C)C)(=O)=O GPQXADGDQZYFMV-UHFFFAOYSA-N 0.000 claims 1
- CSXDJPXXSIMJBX-UHFFFAOYSA-N 2-(5-benzyl-2,2-diethyl-1,3-dioxolan-4-yl)ethyl sulfamate Chemical compound O1C(CC)(CC)OC(CCOS(N)(=O)=O)C1CC1=CC=CC=C1 CSXDJPXXSIMJBX-UHFFFAOYSA-N 0.000 claims 1
- SFNZSFGVNUSPAU-UHFFFAOYSA-N 2-(5-benzyl-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl sulfamate Chemical compound O1C(C)(C)OC(CCOS(N)(=O)=O)C1CC1=CC=CC=C1 SFNZSFGVNUSPAU-UHFFFAOYSA-N 0.000 claims 1
- IQUJYITYUVTFDO-UHFFFAOYSA-N 2-[5-(2-chlorophenyl)-2,2-diethyl-1,3-dioxolan-4-yl]ethyl sulfamate Chemical compound O1C(CC)(CC)OC(CCOS(N)(=O)=O)C1C1=CC=CC=C1Cl IQUJYITYUVTFDO-UHFFFAOYSA-N 0.000 claims 1
- JANMWWVANVYISM-UHFFFAOYSA-N 2-[5-(2-chlorophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl]ethyl sulfamate Chemical compound O1C(C)(C)OC(CCOS(N)(=O)=O)C1C1=CC=CC=C1Cl JANMWWVANVYISM-UHFFFAOYSA-N 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 1
- 206010008025 Cerebellar ataxia Diseases 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 206010019196 Head injury Diseases 0.000 claims 1
- 208000003618 Intervertebral Disc Displacement Diseases 0.000 claims 1
- 206010050296 Intervertebral disc protrusion Diseases 0.000 claims 1
- 206010033799 Paralysis Diseases 0.000 claims 1
- 206010041591 Spinal osteoarthritis Diseases 0.000 claims 1
- 208000010112 Spinocerebellar Degenerations Diseases 0.000 claims 1
- CCEQDWQILIYXES-UHFFFAOYSA-N [2,2-diethyl-5-(2-fluorophenyl)-1,3-dioxolan-4-yl] n-methylsulfamate Chemical compound O1C(CC)(CC)OC(OS(=O)(=O)NC)C1C1=CC=CC=C1F CCEQDWQILIYXES-UHFFFAOYSA-N 0.000 claims 1
- CTXKJOAYNUSUTN-UHFFFAOYSA-N [2,2-diethyl-5-(2-iodophenyl)-1,3-dioxolan-4-yl] n-methylsulfamate Chemical compound O1C(CC)(CC)OC(OS(=O)(=O)NC)C1C1=CC=CC=C1I CTXKJOAYNUSUTN-UHFFFAOYSA-N 0.000 claims 1
- CRGOFPIHIFHLDM-UHFFFAOYSA-N [2,2-diethyl-5-(2-nitrophenyl)-1,3-dioxolan-4-yl] n-methylsulfamate Chemical compound O1C(CC)(CC)OC(OS(=O)(=O)NC)C1C1=CC=CC=C1[N+]([O-])=O CRGOFPIHIFHLDM-UHFFFAOYSA-N 0.000 claims 1
- VYFUJFFIVKNUBI-UHFFFAOYSA-N [2,2-dimethyl-5-(2-nitrophenyl)-1,3-dioxolan-4-yl] n-methylsulfamate Chemical compound CNS(=O)(=O)OC1OC(C)(C)OC1C1=CC=CC=C1[N+]([O-])=O VYFUJFFIVKNUBI-UHFFFAOYSA-N 0.000 claims 1
- IDACWPCWXNMNRT-UHFFFAOYSA-N [2,2-dimethyl-5-[2-(methylamino)phenyl]-1,3-dioxolan-4-yl] n-methylsulfamate Chemical compound CNC1=CC=CC=C1C1C(OS(=O)(=O)NC)OC(C)(C)O1 IDACWPCWXNMNRT-UHFFFAOYSA-N 0.000 claims 1
- HQFOTYLYSLIZRC-UHFFFAOYSA-N [2-(2,4-dichlorophenyl)-1,4-dioxaspiro[4.4]nonan-3-yl] n-methylsulfamate Chemical compound O1C(C=2C(=CC(Cl)=CC=2)Cl)C(OS(=O)(=O)NC)OC21CCCC2 HQFOTYLYSLIZRC-UHFFFAOYSA-N 0.000 claims 1
- HKKBEQNHGMHVGX-UHFFFAOYSA-N [2-(2,4-dichlorophenyl)-1,4-dioxaspiro[4.5]decan-3-yl] n-methylsulfamate Chemical compound O1C(C=2C(=CC(Cl)=CC=2)Cl)C(OS(=O)(=O)NC)OC21CCCCC2 HKKBEQNHGMHVGX-UHFFFAOYSA-N 0.000 claims 1
- ZYUHZEPWRAULIT-UHFFFAOYSA-N [2-(2,6-dichlorophenyl)-1,4-dioxaspiro[4.4]nonan-3-yl] n-methylsulfamate Chemical compound O1C(C=2C(=CC=CC=2Cl)Cl)C(OS(=O)(=O)NC)OC21CCCC2 ZYUHZEPWRAULIT-UHFFFAOYSA-N 0.000 claims 1
- TVMNCJMOXITMPJ-UHFFFAOYSA-N [2-(2,6-dichlorophenyl)-1,4-dioxaspiro[4.5]decan-3-yl] n-methylsulfamate Chemical compound O1C(C=2C(=CC=CC=2Cl)Cl)C(OS(=O)(=O)NC)OC21CCCCC2 TVMNCJMOXITMPJ-UHFFFAOYSA-N 0.000 claims 1
- IIIFWODIVCBODB-UHFFFAOYSA-N [2-(2-aminophenyl)-1,4-dioxaspiro[4.4]nonan-3-yl] n-methylsulfamate Chemical compound O1C(C=2C(=CC=CC=2)N)C(OS(=O)(=O)NC)OC21CCCC2 IIIFWODIVCBODB-UHFFFAOYSA-N 0.000 claims 1
- LWPMLINGYGTOFK-UHFFFAOYSA-N [2-(2-aminophenyl)-1,4-dioxaspiro[4.5]decan-3-yl] n-methylsulfamate Chemical compound O1C(C=2C(=CC=CC=2)N)C(OS(=O)(=O)NC)OC21CCCCC2 LWPMLINGYGTOFK-UHFFFAOYSA-N 0.000 claims 1
- WMZCTAMDLDIKSL-UHFFFAOYSA-N [2-(2-chlorophenyl)-1,4-dioxaspiro[4.4]nonan-3-yl] n-methylsulfamate Chemical compound O1C(C=2C(=CC=CC=2)Cl)C(OS(=O)(=O)NC)OC21CCCC2 WMZCTAMDLDIKSL-UHFFFAOYSA-N 0.000 claims 1
- YPBUVTCWMAYZKN-UHFFFAOYSA-N [2-(2-fluorophenyl)-1,4-dioxaspiro[4.4]nonan-3-yl] n-methylsulfamate Chemical compound O1C(C=2C(=CC=CC=2)F)C(OS(=O)(=O)NC)OC21CCCC2 YPBUVTCWMAYZKN-UHFFFAOYSA-N 0.000 claims 1
- KHJKCKSTCJYDBW-UHFFFAOYSA-N [2-(2-fluorophenyl)-1,4-dioxaspiro[4.5]decan-3-yl] n-methylsulfamate Chemical compound O1C(C=2C(=CC=CC=2)F)C(OS(=O)(=O)NC)OC21CCCCC2 KHJKCKSTCJYDBW-UHFFFAOYSA-N 0.000 claims 1
- KMXRXDHYNNLLNT-UHFFFAOYSA-N [2-(2-iodophenyl)-1,4-dioxaspiro[4.4]nonan-3-yl] n-methylsulfamate Chemical compound O1C(C=2C(=CC=CC=2)I)C(OS(=O)(=O)NC)OC21CCCC2 KMXRXDHYNNLLNT-UHFFFAOYSA-N 0.000 claims 1
- AQKHZHZWWGIUTI-UHFFFAOYSA-N [2-(2-iodophenyl)-1,4-dioxaspiro[4.5]decan-3-yl] n-methylsulfamate Chemical compound O1C(C=2C(=CC=CC=2)I)C(OS(=O)(=O)NC)OC21CCCCC2 AQKHZHZWWGIUTI-UHFFFAOYSA-N 0.000 claims 1
- COIYAPLKXQPPFJ-UHFFFAOYSA-N [2-(2-methylphenyl)-1,4-dioxaspiro[4.4]nonan-3-yl] n-methylsulfamate Chemical compound O1C(C=2C(=CC=CC=2)C)C(OS(=O)(=O)NC)OC21CCCC2 COIYAPLKXQPPFJ-UHFFFAOYSA-N 0.000 claims 1
- LBUAQTUYQANDDV-UHFFFAOYSA-N [2-(2-methylphenyl)-1,4-dioxaspiro[4.5]decan-3-yl] n-methylsulfamate Chemical compound O1C(C=2C(=CC=CC=2)C)C(OS(=O)(=O)NC)OC21CCCCC2 LBUAQTUYQANDDV-UHFFFAOYSA-N 0.000 claims 1
- XAFLZQUXVVHOED-UHFFFAOYSA-N [2-(2-nitrophenyl)-1,4-dioxaspiro[4.4]nonan-3-yl] n-methylsulfamate Chemical compound O1C(C=2C(=CC=CC=2)[N+]([O-])=O)C(OS(=O)(=O)NC)OC21CCCC2 XAFLZQUXVVHOED-UHFFFAOYSA-N 0.000 claims 1
- NWIIZLPCMXEDLP-UHFFFAOYSA-N [2-(2-nitrophenyl)-1,4-dioxaspiro[4.5]decan-3-yl] n-methylsulfamate Chemical compound O1C(C=2C(=CC=CC=2)[N+]([O-])=O)C(OS(=O)(=O)NC)OC21CCCCC2 NWIIZLPCMXEDLP-UHFFFAOYSA-N 0.000 claims 1
- IEVLMWVYCWAGAM-UHFFFAOYSA-N [2-[(2-chlorophenyl)methyl]-1,4-dioxaspiro[4.4]nonan-3-yl] N-methylsulfamate Chemical compound CNS(OC1OC2(OC1CC1=C(C=CC=C1)Cl)CCCC2)(=O)=O IEVLMWVYCWAGAM-UHFFFAOYSA-N 0.000 claims 1
- BKIKAYGOQDQWGP-UHFFFAOYSA-N [2-[(2-chlorophenyl)methyl]-1,4-dioxaspiro[4.5]decan-3-yl] N-methylsulfamate Chemical compound CNS(OC1OC2(OC1CC1=C(C=CC=C1)Cl)CCCCC2)(=O)=O BKIKAYGOQDQWGP-UHFFFAOYSA-N 0.000 claims 1
- XSVTYWOUHAZWIV-UHFFFAOYSA-N [2-methyl-5-(2-methylphenyl)-1,3-dioxolan-4-yl] n-methylsulfamate Chemical compound CNS(=O)(=O)OC1OC(C)OC1C1=CC=CC=C1C XSVTYWOUHAZWIV-UHFFFAOYSA-N 0.000 claims 1
- FETXOOSBVWOELJ-UHFFFAOYSA-N [2-methyl-5-(2-nitrophenyl)-1,3-dioxolan-4-yl] n-methylsulfamate Chemical compound CNS(=O)(=O)OC1OC(C)OC1C1=CC=CC=C1[N+]([O-])=O FETXOOSBVWOELJ-UHFFFAOYSA-N 0.000 claims 1
- XNPNIYWWVGGUIK-UHFFFAOYSA-N [5-(2,4-dichlorophenyl)-2,2-diethyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound O1C(CC)(CC)OC(COS(N)(=O)=O)C1C1=CC=C(Cl)C=C1Cl XNPNIYWWVGGUIK-UHFFFAOYSA-N 0.000 claims 1
- PZJPBLBSIBZHEU-UHFFFAOYSA-N [5-(2,4-dichlorophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound O1C(C)(C)OC(COS(N)(=O)=O)C1C1=CC=C(Cl)C=C1Cl PZJPBLBSIBZHEU-UHFFFAOYSA-N 0.000 claims 1
- VAYHBFLVNBUIQJ-UHFFFAOYSA-N [5-(2,4-dichlorophenyl)-2-methyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound O1C(C)OC(COS(N)(=O)=O)C1C1=CC=C(Cl)C=C1Cl VAYHBFLVNBUIQJ-UHFFFAOYSA-N 0.000 claims 1
- QPUZPKPURUDSKT-UHFFFAOYSA-N [5-(2,4-dichlorophenyl)-2-phenyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound NS(=O)(=O)OCC1OC(C=2C=CC=CC=2)OC1C1=CC=C(Cl)C=C1Cl QPUZPKPURUDSKT-UHFFFAOYSA-N 0.000 claims 1
- VATHXICLBXMRAO-UHFFFAOYSA-N [5-(2,6-dichlorophenyl)-2,2-diethyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound O1C(CC)(CC)OC(COS(N)(=O)=O)C1C1=C(Cl)C=CC=C1Cl VATHXICLBXMRAO-UHFFFAOYSA-N 0.000 claims 1
- ZCCGKLLDFDGOMF-UHFFFAOYSA-N [5-(2,6-dichlorophenyl)-2-methyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound O1C(C)OC(COS(N)(=O)=O)C1C1=C(Cl)C=CC=C1Cl ZCCGKLLDFDGOMF-UHFFFAOYSA-N 0.000 claims 1
- UDZGOSZSFMSKDM-UHFFFAOYSA-N [5-(2,6-dichlorophenyl)-2-phenyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound NS(=O)(=O)OCC1OC(C=2C=CC=CC=2)OC1C1=C(Cl)C=CC=C1Cl UDZGOSZSFMSKDM-UHFFFAOYSA-N 0.000 claims 1
- MOUITVGTOGQRGR-UHFFFAOYSA-N [5-(2-aminophenyl)-2,2-diethyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound O1C(CC)(CC)OC(COS(N)(=O)=O)C1C1=CC=CC=C1N MOUITVGTOGQRGR-UHFFFAOYSA-N 0.000 claims 1
- PPMVXZLGSOOHNV-UHFFFAOYSA-N [5-(2-aminophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound O1C(C)(C)OC(COS(N)(=O)=O)C1C1=CC=CC=C1N PPMVXZLGSOOHNV-UHFFFAOYSA-N 0.000 claims 1
- LNUSHCOTFXLBNS-UHFFFAOYSA-N [5-(2-aminophenyl)-2-methyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound O1C(C)OC(COS(N)(=O)=O)C1C1=CC=CC=C1N LNUSHCOTFXLBNS-UHFFFAOYSA-N 0.000 claims 1
- PKNWMDOCDWBNCK-UHFFFAOYSA-N [5-(2-aminophenyl)-2-phenyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound NC1=CC=CC=C1C1C(COS(N)(=O)=O)OC(C=2C=CC=CC=2)O1 PKNWMDOCDWBNCK-UHFFFAOYSA-N 0.000 claims 1
- UANGRXRESSDGEE-UHFFFAOYSA-N [5-(2-chlorophenyl)-2-phenyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound NS(=O)(=O)OCC1OC(C=2C=CC=CC=2)OC1C1=CC=CC=C1Cl UANGRXRESSDGEE-UHFFFAOYSA-N 0.000 claims 1
- ANYUUFVAPYZBOM-UHFFFAOYSA-N [5-(2-fluorophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound O1C(C)(C)OC(COS(N)(=O)=O)C1C1=CC=CC=C1F ANYUUFVAPYZBOM-UHFFFAOYSA-N 0.000 claims 1
- ZUBCNBYVKBJOHW-UHFFFAOYSA-N [5-(2-fluorophenyl)-2-methyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound S(N)(OCC1OC(OC1C1=C(C=CC=C1)F)C)(=O)=O ZUBCNBYVKBJOHW-UHFFFAOYSA-N 0.000 claims 1
- PGKJDCCMJALRSH-UHFFFAOYSA-N [5-(2-fluorophenyl)-2-phenyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound NS(=O)(=O)OCC1OC(C=2C=CC=CC=2)OC1C1=CC=CC=C1F PGKJDCCMJALRSH-UHFFFAOYSA-N 0.000 claims 1
- DVWFSTVNQGCQOW-UHFFFAOYSA-N [5-(2-iodophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound O1C(C)(C)OC(COS(N)(=O)=O)C1C1=CC=CC=C1I DVWFSTVNQGCQOW-UHFFFAOYSA-N 0.000 claims 1
- SSQLUTKYINNSAY-UHFFFAOYSA-N [5-(2-iodophenyl)-2-methyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound S(N)(OCC1OC(OC1C1=C(C=CC=C1)I)C)(=O)=O SSQLUTKYINNSAY-UHFFFAOYSA-N 0.000 claims 1
- BDHJUEFXZRDXKT-UHFFFAOYSA-N [5-(2-iodophenyl)-2-phenyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound NS(=O)(=O)OCC1OC(C=2C=CC=CC=2)OC1C1=CC=CC=C1I BDHJUEFXZRDXKT-UHFFFAOYSA-N 0.000 claims 1
- LFJHTCHBWSCVIF-UHFFFAOYSA-N [5-(2-methylphenyl)-2-phenyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound CC1=CC=CC=C1C1C(COS(N)(=O)=O)OC(C=2C=CC=CC=2)O1 LFJHTCHBWSCVIF-UHFFFAOYSA-N 0.000 claims 1
- QXXREHAVUAFLBD-UHFFFAOYSA-N [5-(2-nitrophenyl)-2-phenyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound NS(=O)(=O)OCC1OC(C=2C=CC=CC=2)OC1C1=CC=CC=C1[N+]([O-])=O QXXREHAVUAFLBD-UHFFFAOYSA-N 0.000 claims 1
- PBRUIZBRZKWNML-UHFFFAOYSA-N [5-[(2-chlorophenyl)methyl]-2,2-diethyl-1,3-dioxolan-4-yl] N-methylsulfamate Chemical compound CNS(OC1OC(OC1CC1=C(C=CC=C1)Cl)(CC)CC)(=O)=O PBRUIZBRZKWNML-UHFFFAOYSA-N 0.000 claims 1
- JGHPPZGFMDDXGM-UHFFFAOYSA-N [5-[(2-chlorophenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl] N-methylsulfamate Chemical compound CNS(OC1OC(OC1CC1=C(C=CC=C1)Cl)(C)C)(=O)=O JGHPPZGFMDDXGM-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 206010008129 cerebral palsy Diseases 0.000 claims 1
- 208000036319 cervical spondylosis Diseases 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 238000005906 dihydroxylation reaction Methods 0.000 claims 1
- BGGQCYYULFFRLC-UHFFFAOYSA-N ethyl sulfamate Chemical compound CCOS(N)(=O)=O BGGQCYYULFFRLC-UHFFFAOYSA-N 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- FIYXUOWXHWJDAM-UHFFFAOYSA-N methyl sulfamate Chemical compound COS(N)(=O)=O FIYXUOWXHWJDAM-UHFFFAOYSA-N 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 230000001148 spastic effect Effects 0.000 claims 1
- 210000000278 spinal cord Anatomy 0.000 claims 1
- 208000020431 spinal cord injury Diseases 0.000 claims 1
- 208000005801 spondylosis Diseases 0.000 claims 1
- 208000019553 vascular disease Diseases 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261660064P | 2012-06-15 | 2012-06-15 | |
| US61/660,064 | 2012-06-15 | ||
| PCT/KR2013/005279 WO2013187727A1 (en) | 2012-06-15 | 2013-06-14 | Phenylalkyl sulfamate compound and muscle relaxant composition comprising the same |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015531746A JP2015531746A (ja) | 2015-11-05 |
| JP2015531746A5 true JP2015531746A5 (enExample) | 2016-06-16 |
| JP6001168B2 JP6001168B2 (ja) | 2016-10-05 |
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| JP2015517189A Active JP6001168B2 (ja) | 2012-06-15 | 2013-06-14 | フェニルアルキルスルファメート化合物及びこれを含む筋弛緩剤組成物 |
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| ES (1) | ES2635067T3 (enExample) |
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| WO2015088272A1 (en) | 2013-12-12 | 2015-06-18 | Bio-Pharm Solutions Co., Ltd. | Sulfamate derivative compounds for use in treating or alleviating pain |
| US9937145B2 (en) * | 2013-12-12 | 2018-04-10 | Bio-Pharm Solutions Co., Ltd. | Sulfamate derivative compound for use in preventing or treating epilepsy |
| ES2704928T3 (es) | 2013-12-12 | 2019-03-20 | Bio Pharm Solutions Co Ltd | Compuestos derivados de sulfamato para su uso en el tratamiento o alivio del dolor |
| US11896593B2 (en) * | 2020-09-10 | 2024-02-13 | Bio-Pharm Solutions Co., Ltd. | Sulfamate derivative compounds for use in treating or alleviating a psychiatric disorder |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US459160A (en) * | 1891-09-08 | Half to isaac l | ||
| US2884444A (en) | 1956-01-13 | 1959-04-28 | Carter Prod Inc | 2-phenyl-1,3 propane diol dicarbamate |
| US2937119A (en) | 1959-06-11 | 1960-05-17 | Carter Prod Inc | Nu-monosubstituted-2, 2-dialkyl-1, 3-propanediol dicarbamates |
| US3313692A (en) | 1958-04-21 | 1967-04-11 | Armour Pharma | Method of inducing calming and muscle relaxation with carbamates |
| US3265727A (en) | 1962-06-26 | 1966-08-09 | Armour Pharma | Phenyl alkyl-1, 2 dicarbamates |
| US4591601A (en) | 1985-04-12 | 1986-05-27 | Mcneilab, Inc. | Anticonvulsant dioxolane methane sulfamates |
| US4792569A (en) | 1987-08-27 | 1988-12-20 | Mcneilab, Inc. | Anticonvulsant phenethyl sulfamates |
| US5025031A (en) | 1989-11-30 | 1991-06-18 | A. H. Robins Co., Inc. | Aryl and aryloxyalkyl sulfamate esters useful as anticonvulsants |
| JPH05140144A (ja) * | 1991-11-14 | 1993-06-08 | Nitto Denko Corp | 新規なアルコール及びその製法、及び新規なエステル並びにこの新規なアルコールからニンジン類の発根誘起物質を製造する方法 |
| JPH07228549A (ja) * | 1994-02-17 | 1995-08-29 | Japan Tobacco Inc | 新規な４−アリール−２，３−ジヒドロキシ酪酸誘導体及びその製造方法 |
| JP4145492B2 (ja) * | 1998-09-23 | 2008-09-03 | ニコメッド ゲゼルシャフト ミット ベシュレンクテル ハフツング | テトラヒドロピリドエーテル |
| IS7839A (is) * | 2002-11-22 | 2004-05-23 | Merck Frosst Canada Ltd. | 4-oxó-1-(3-setið fenýl-1,4-díhýdró-1,8-naftýridín-3-karboxamíð fosfódíesterasa-4 hindrar |
| US20050192286A1 (en) | 2003-10-22 | 2005-09-01 | Neurocrine Biosciences, Inc. | Ligands of melanocortin receptors and compositions and methods related thereto |
| WO2007005935A2 (en) * | 2005-07-06 | 2007-01-11 | Molecular Neuroimaging, Llc | Norepinephrine transporter radiotracers and methods of syntheses thereof |
| EP1945651B1 (en) * | 2005-10-25 | 2014-06-25 | The Ludwig Institute for Cancer Research | Analogs of alpha galactosylceramide and uses thereof |
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2013
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- 2013-06-14 EP EP13803704.9A patent/EP2861571B1/en active Active
- 2013-06-14 BR BR112014031396A patent/BR112014031396B1/pt active IP Right Grant
- 2013-06-14 KR KR1020147035195A patent/KR101699145B1/ko active Active
- 2013-06-14 ES ES13803704.9T patent/ES2635067T3/es active Active
- 2013-06-14 CA CA2874988A patent/CA2874988C/en active Active
- 2013-06-14 CN CN201380031295.2A patent/CN104428292B/zh active Active
- 2013-06-14 WO PCT/KR2013/005279 patent/WO2013187727A1/en not_active Ceased
- 2013-06-14 US US14/401,990 patent/US9221783B2/en active Active
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