CA2874988C - Phenylalkyl sulfamate compound and muscle relaxant composition comprising the same - Google Patents
Phenylalkyl sulfamate compound and muscle relaxant composition comprising the same Download PDFInfo
- Publication number
- CA2874988C CA2874988C CA2874988A CA2874988A CA2874988C CA 2874988 C CA2874988 C CA 2874988C CA 2874988 A CA2874988 A CA 2874988A CA 2874988 A CA2874988 A CA 2874988A CA 2874988 C CA2874988 C CA 2874988C
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- CA
- Canada
- Prior art keywords
- preparation example
- dioxolan
- methyl
- dioxaspiro
- sulfamate
- 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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- -1 Phenylalkyl sulfamate compound Chemical class 0.000 title claims abstract description 29
- 239000000203 mixture Substances 0.000 title claims description 59
- 239000003158 myorelaxant agent Substances 0.000 title description 10
- 238000000034 method Methods 0.000 claims abstract description 525
- 208000005392 Spasm Diseases 0.000 claims abstract description 23
- 208000007101 Muscle Cramp Diseases 0.000 claims abstract description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 22
- 201000010099 disease Diseases 0.000 claims abstract description 20
- 206010021118 Hypotonia Diseases 0.000 claims abstract description 18
- 230000036640 muscle relaxation Effects 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims description 636
- FIYXUOWXHWJDAM-UHFFFAOYSA-N methyl sulfamate Chemical compound COS(N)(=O)=O FIYXUOWXHWJDAM-UHFFFAOYSA-N 0.000 claims description 190
- 150000003839 salts Chemical class 0.000 claims description 27
- 239000000460 chlorine Substances 0.000 claims description 20
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 238000005906 dihydroxylation reaction Methods 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- UFAQBDPKMLFYOJ-UHFFFAOYSA-N (3-phenyl-1,4-dioxaspiro[4.4]nonan-2-yl)methyl sulfamate Chemical compound O1C(C=2C=CC=CC=2)C(COS(=O)(=O)N)OC21CCCC2 UFAQBDPKMLFYOJ-UHFFFAOYSA-N 0.000 claims description 7
- 239000007800 oxidant agent Substances 0.000 claims description 7
- 230000001590 oxidative effect Effects 0.000 claims description 7
- PAGKZDRQDAMJEO-UHFFFAOYSA-N (2,2-diethyl-5-phenyl-1,3-dioxolan-4-yl)methyl sulfamate Chemical compound O1C(CC)(CC)OC(COS(N)(=O)=O)C1C1=CC=CC=C1 PAGKZDRQDAMJEO-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 206010019196 Head injury Diseases 0.000 claims description 5
- 239000003638 chemical reducing agent Substances 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 210000000278 spinal cord Anatomy 0.000 claims description 5
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
- 206010041591 Spinal osteoarthritis Diseases 0.000 claims description 4
- 125000003277 amino group Chemical class 0.000 claims description 4
- 150000001721 carbon Chemical group 0.000 claims description 4
- 206010008129 cerebral palsy Diseases 0.000 claims description 4
- 208000036319 cervical spondylosis Diseases 0.000 claims description 4
- 208000020431 spinal cord injury Diseases 0.000 claims description 4
- 208000005801 spondylosis Diseases 0.000 claims description 4
- 208000019553 vascular disease Diseases 0.000 claims description 4
- HDFHHRANIYFXMG-UHFFFAOYSA-N (3-phenyl-1,4-dioxaspiro[4.5]decan-2-yl)methyl sulfamate Chemical compound O1C(C=2C=CC=CC=2)C(COS(=O)(=O)N)OC21CCCCC2 HDFHHRANIYFXMG-UHFFFAOYSA-N 0.000 claims description 3
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
- 206010008025 Cerebellar ataxia Diseases 0.000 claims description 3
- 206010033799 Paralysis Diseases 0.000 claims description 3
- 208000010112 Spinocerebellar Degenerations Diseases 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 150000001413 amino acids Chemical class 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 230000001148 spastic effect Effects 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- WBYFNFZBLNVURP-UHFFFAOYSA-N 2-(2,2-diethyl-5-phenyl-1,3-dioxolan-4-yl)ethyl sulfamate Chemical compound O1C(CC)(CC)OC(CCOS(N)(=O)=O)C1C1=CC=CC=C1 WBYFNFZBLNVURP-UHFFFAOYSA-N 0.000 claims 2
- YVKXZAIIVYNEOO-UHFFFAOYSA-N [2,2-dimethyl-5-(2-methylphenyl)-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound CC1=CC=CC=C1C1C(COS(N)(=O)=O)OC(C)(C)O1 YVKXZAIIVYNEOO-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
- PBROIEAOSQDSKL-UHFFFAOYSA-N (2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl)methyl sulfamate Chemical compound O1C(C)(C)OC(COS(N)(=O)=O)C1C1=CC=CC=C1 PBROIEAOSQDSKL-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
- HVPUOMSKEBVERQ-UHFFFAOYSA-N 2-(2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl)ethyl sulfamate Chemical compound O1C(C)(C)OC(CCOS(N)(=O)=O)C1C1=CC=CC=C1 HVPUOMSKEBVERQ-UHFFFAOYSA-N 0.000 claims 1
- PXTWHSGPPMDOIG-UHFFFAOYSA-N 2-(3-benzyl-1,4-dioxaspiro[4.5]decan-2-yl)ethyl sulfamate Chemical compound O1C(CC=2C=CC=CC=2)C(CCOS(=O)(=O)N)OC21CCCCC2 PXTWHSGPPMDOIG-UHFFFAOYSA-N 0.000 claims 1
- BHGFSUBKDVBPDT-UHFFFAOYSA-N 2-(3-phenyl-1,4-dioxaspiro[4.4]nonan-2-yl)ethyl sulfamate Chemical compound O1C(C=2C=CC=CC=2)C(CCOS(=O)(=O)N)OC21CCCC2 BHGFSUBKDVBPDT-UHFFFAOYSA-N 0.000 claims 1
- IMNQDVVJBVTSJR-UHFFFAOYSA-N 2-(3-phenyl-1,4-dioxaspiro[4.5]decan-2-yl)ethyl sulfamate Chemical compound O1C(C=2C=CC=CC=2)C(CCOS(=O)(=O)N)OC21CCCCC2 IMNQDVVJBVTSJR-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
- IDCRWWJQMDMCQE-UHFFFAOYSA-N 2-[3-(2-chlorophenyl)-1,4-dioxaspiro[4.4]nonan-2-yl]ethyl sulfamate Chemical compound O1C(C=2C(=CC=CC=2)Cl)C(CCOS(=O)(=O)N)OC21CCCC2 IDCRWWJQMDMCQE-UHFFFAOYSA-N 0.000 claims 1
- VCIFGTAEWMNJHQ-UHFFFAOYSA-N 2-[3-(2-chlorophenyl)-1,4-dioxaspiro[4.5]decan-2-yl]ethyl sulfamate Chemical compound O1C(C=2C(=CC=CC=2)Cl)C(CCOS(=O)(=O)N)OC21CCCCC2 VCIFGTAEWMNJHQ-UHFFFAOYSA-N 0.000 claims 1
- AIWSCVQUUGBBDT-UHFFFAOYSA-N 2-[3-[(2-chlorophenyl)methyl]-1,4-dioxaspiro[4.4]nonan-2-yl]ethyl sulfamate Chemical compound O1C(CC=2C(=CC=CC=2)Cl)C(CCOS(=O)(=O)N)OC21CCCC2 AIWSCVQUUGBBDT-UHFFFAOYSA-N 0.000 claims 1
- OPAWQWIZBMCMPZ-UHFFFAOYSA-N 2-[3-[(2-chlorophenyl)methyl]-1,4-dioxaspiro[4.5]decan-2-yl]ethyl sulfamate Chemical compound O1C(CC=2C(=CC=CC=2)Cl)C(CCOS(=O)(=O)N)OC21CCCCC2 OPAWQWIZBMCMPZ-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
- WSXNPBPOVWHADO-UHFFFAOYSA-N 2-[5-[(2-chlorophenyl)methyl]-2,2-diethyl-1,3-dioxolan-4-yl]ethyl sulfamate Chemical compound O1C(CC)(CC)OC(CCOS(N)(=O)=O)C1CC1=CC=CC=C1Cl WSXNPBPOVWHADO-UHFFFAOYSA-N 0.000 claims 1
- AROMUOUFPZOGSN-UHFFFAOYSA-N 2-[5-[(2-chlorophenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]ethyl sulfamate Chemical compound O1C(C)(C)OC(CCOS(N)(=O)=O)C1CC1=CC=CC=C1Cl AROMUOUFPZOGSN-UHFFFAOYSA-N 0.000 claims 1
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 1
- CFDDNVAZJWAEFX-UHFFFAOYSA-N S(N)(OCC1OC(OC1CC1=C(C=CC=C1)Cl)(C)C)(=O)=O Chemical compound S(N)(OCC1OC(OC1CC1=C(C=CC=C1)Cl)(C)C)(=O)=O CFDDNVAZJWAEFX-UHFFFAOYSA-N 0.000 claims 1
- QOBDIIQWAXTPTM-UHFFFAOYSA-N S(N)(OCC1OC(OC1CC1=C(C=CC=C1)Cl)(CC)CC)(=O)=O Chemical compound S(N)(OCC1OC(OC1CC1=C(C=CC=C1)Cl)(CC)CC)(=O)=O QOBDIIQWAXTPTM-UHFFFAOYSA-N 0.000 claims 1
- UFAIJJPGMXRUMJ-UHFFFAOYSA-N S(N)(OCC1OC2(OC1CC1=C(C=CC=C1)Cl)CCCC2)(=O)=O Chemical compound S(N)(OCC1OC2(OC1CC1=C(C=CC=C1)Cl)CCCC2)(=O)=O UFAIJJPGMXRUMJ-UHFFFAOYSA-N 0.000 claims 1
- IIIAPVABXZRPLO-UHFFFAOYSA-N S(N)(OCC1OC2(OC1CC1=C(C=CC=C1)Cl)CCCCC2)(=O)=O Chemical compound S(N)(OCC1OC2(OC1CC1=C(C=CC=C1)Cl)CCCCC2)(=O)=O IIIAPVABXZRPLO-UHFFFAOYSA-N 0.000 claims 1
- NBHCHKGMMWFVSC-UHFFFAOYSA-N S(N)(OCC1OC2(OC1CC1=CC=CC=C1)CCCC2)(=O)=O Chemical compound S(N)(OCC1OC2(OC1CC1=CC=CC=C1)CCCC2)(=O)=O NBHCHKGMMWFVSC-UHFFFAOYSA-N 0.000 claims 1
- FJEORNRCXSIAFD-UHFFFAOYSA-N S(N)(OCC1OC2(OC1CC1=CC=CC=C1)CCCCC2)(=O)=O Chemical compound S(N)(OCC1OC2(OC1CC1=CC=CC=C1)CCCCC2)(=O)=O FJEORNRCXSIAFD-UHFFFAOYSA-N 0.000 claims 1
- XZBZECPDTISWHC-UHFFFAOYSA-N S(N)(OCCC1OC2(OC1CC1=CC=CC=C1)CCCC2)(=O)=O Chemical compound S(N)(OCCC1OC2(OC1CC1=CC=CC=C1)CCCC2)(=O)=O XZBZECPDTISWHC-UHFFFAOYSA-N 0.000 claims 1
- JPMYANDQVOVWAP-UHFFFAOYSA-N [2,2-diethyl-5-(2-fluorophenyl)-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound O1C(CC)(CC)OC(COS(N)(=O)=O)C1C1=CC=CC=C1F JPMYANDQVOVWAP-UHFFFAOYSA-N 0.000 claims 1
- CZHYZNGDIYUYFF-UHFFFAOYSA-N [2,2-diethyl-5-(2-methylphenyl)-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound O1C(CC)(CC)OC(COS(N)(=O)=O)C1C1=CC=CC=C1C CZHYZNGDIYUYFF-UHFFFAOYSA-N 0.000 claims 1
- BGIWHWOMNPCRTM-UHFFFAOYSA-N [2,2-diethyl-5-(2-nitrophenyl)-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound O1C(CC)(CC)OC(COS(N)(=O)=O)C1C1=CC=CC=C1[N+]([O-])=O BGIWHWOMNPCRTM-UHFFFAOYSA-N 0.000 claims 1
- PTEGAVAMIJECNM-UHFFFAOYSA-N [2,2-dimethyl-5-(2-nitrophenyl)-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound O1C(C)(C)OC(COS(N)(=O)=O)C1C1=CC=CC=C1[N+]([O-])=O PTEGAVAMIJECNM-UHFFFAOYSA-N 0.000 claims 1
- OZTIDDRPDJGAQD-UHFFFAOYSA-N [2-methyl-5-(2-methylphenyl)-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound O1C(C)OC(COS(N)(=O)=O)C1C1=CC=CC=C1C OZTIDDRPDJGAQD-UHFFFAOYSA-N 0.000 claims 1
- VEHHQWKPDSXNLH-UHFFFAOYSA-N [3-(2,4-dichlorophenyl)-1,4-dioxaspiro[4.4]nonan-2-yl]methyl sulfamate Chemical compound O1C(C=2C(=CC(Cl)=CC=2)Cl)C(COS(=O)(=O)N)OC21CCCC2 VEHHQWKPDSXNLH-UHFFFAOYSA-N 0.000 claims 1
- PSSAFWFYBZVIOF-UHFFFAOYSA-N [3-(2,4-dichlorophenyl)-1,4-dioxaspiro[4.5]decan-2-yl]methyl sulfamate Chemical compound O1C(C=2C(=CC(Cl)=CC=2)Cl)C(COS(=O)(=O)N)OC21CCCCC2 PSSAFWFYBZVIOF-UHFFFAOYSA-N 0.000 claims 1
- XRSOPXCSISXFET-UHFFFAOYSA-N [3-(2,6-dichlorophenyl)-1,4-dioxaspiro[4.4]nonan-2-yl]methyl sulfamate Chemical compound O1C(C=2C(=CC=CC=2Cl)Cl)C(COS(=O)(=O)N)OC21CCCC2 XRSOPXCSISXFET-UHFFFAOYSA-N 0.000 claims 1
- HPJNPYKOJAELQJ-UHFFFAOYSA-N [3-(2,6-dichlorophenyl)-1,4-dioxaspiro[4.5]decan-2-yl]methyl sulfamate Chemical compound O1C(C=2C(=CC=CC=2Cl)Cl)C(COS(=O)(=O)N)OC21CCCCC2 HPJNPYKOJAELQJ-UHFFFAOYSA-N 0.000 claims 1
- UUNCBDKHARILDM-UHFFFAOYSA-N [3-(2-aminophenyl)-1,4-dioxaspiro[4.4]nonan-2-yl]methyl sulfamate Chemical compound NC1=CC=CC=C1C1C(COS(N)(=O)=O)OC2(CCCC2)O1 UUNCBDKHARILDM-UHFFFAOYSA-N 0.000 claims 1
- KIMGHWUIMAQQBF-UHFFFAOYSA-N [3-(2-aminophenyl)-1,4-dioxaspiro[4.5]decan-2-yl]methyl sulfamate Chemical compound NC1=CC=CC=C1C1C(COS(N)(=O)=O)OC2(CCCCC2)O1 KIMGHWUIMAQQBF-UHFFFAOYSA-N 0.000 claims 1
- AIAKXOMMDHHMII-UHFFFAOYSA-N [3-(2-chlorophenyl)-1,4-dioxaspiro[4.4]nonan-2-yl]methyl sulfamate Chemical compound O1C(C=2C(=CC=CC=2)Cl)C(COS(=O)(=O)N)OC21CCCC2 AIAKXOMMDHHMII-UHFFFAOYSA-N 0.000 claims 1
- FSLSSEGOOBAYRB-UHFFFAOYSA-N [3-(2-chlorophenyl)-1,4-dioxaspiro[4.5]decan-2-yl]methyl sulfamate Chemical compound O1C(C=2C(=CC=CC=2)Cl)C(COS(=O)(=O)N)OC21CCCCC2 FSLSSEGOOBAYRB-UHFFFAOYSA-N 0.000 claims 1
- VKMLNJFIOWLBLW-UHFFFAOYSA-N [3-(2-fluorophenyl)-1,4-dioxaspiro[4.4]nonan-2-yl]methyl sulfamate Chemical compound O1C(C=2C(=CC=CC=2)F)C(COS(=O)(=O)N)OC21CCCC2 VKMLNJFIOWLBLW-UHFFFAOYSA-N 0.000 claims 1
- DHBNMEYGMPWHNM-UHFFFAOYSA-N [3-(2-fluorophenyl)-1,4-dioxaspiro[4.5]decan-2-yl]methyl sulfamate Chemical compound O1C(C=2C(=CC=CC=2)F)C(COS(=O)(=O)N)OC21CCCCC2 DHBNMEYGMPWHNM-UHFFFAOYSA-N 0.000 claims 1
- PQOMUKCQVKFGGI-UHFFFAOYSA-N [3-(2-iodophenyl)-1,4-dioxaspiro[4.5]decan-2-yl]methyl sulfamate Chemical compound O1C(C=2C(=CC=CC=2)I)C(COS(=O)(=O)N)OC21CCCCC2 PQOMUKCQVKFGGI-UHFFFAOYSA-N 0.000 claims 1
- GNPZPINLHJAQRW-UHFFFAOYSA-N [3-(2-methylphenyl)-1,4-dioxaspiro[4.4]nonan-2-yl]methyl sulfamate Chemical compound CC1=CC=CC=C1C1C(COS(N)(=O)=O)OC2(CCCC2)O1 GNPZPINLHJAQRW-UHFFFAOYSA-N 0.000 claims 1
- RIKXSODXARHKGD-UHFFFAOYSA-N [3-(2-methylphenyl)-1,4-dioxaspiro[4.5]decan-2-yl]methyl sulfamate Chemical compound CC1=CC=CC=C1C1C(COS(N)(=O)=O)OC2(CCCCC2)O1 RIKXSODXARHKGD-UHFFFAOYSA-N 0.000 claims 1
- PWLOBFIKXWTAKE-UHFFFAOYSA-N [3-(2-nitrophenyl)-1,4-dioxaspiro[4.4]nonan-2-yl]methyl sulfamate Chemical compound O1C(C=2C(=CC=CC=2)[N+]([O-])=O)C(COS(=O)(=O)N)OC21CCCC2 PWLOBFIKXWTAKE-UHFFFAOYSA-N 0.000 claims 1
- MFMQLDMVNMQFBA-UHFFFAOYSA-N [3-(2-nitrophenyl)-1,4-dioxaspiro[4.5]decan-2-yl]methyl sulfamate Chemical compound O1C(C=2C(=CC=CC=2)[N+]([O-])=O)C(COS(=O)(=O)N)OC21CCCCC2 MFMQLDMVNMQFBA-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
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Classifications
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- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
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- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/28—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D317/34—Oxygen atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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 (2)
| Publication Number | Publication Date |
|---|---|
| CA2874988A1 CA2874988A1 (en) | 2013-12-19 |
| CA2874988C true CA2874988C (en) | 2016-05-24 |
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| CA2874988A Active CA2874988C (en) | 2012-06-15 | 2013-06-14 | Phenylalkyl sulfamate compound and muscle relaxant composition comprising the same |
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|---|---|
| US (1) | US9221783B2 (enExample) |
| EP (1) | EP2861571B1 (enExample) |
| JP (1) | JP6001168B2 (enExample) |
| KR (1) | KR101699145B1 (enExample) |
| CN (1) | CN104428292B (enExample) |
| BR (1) | BR112014031396B1 (enExample) |
| CA (1) | CA2874988C (enExample) |
| ES (1) | ES2635067T3 (enExample) |
| WO (1) | WO2013187727A1 (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
Also Published As
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|---|---|
| EP2861571A1 (en) | 2015-04-22 |
| EP2861571A4 (en) | 2015-11-04 |
| BR112014031396B1 (pt) | 2019-11-26 |
| BR112014031396A2 (pt) | 2017-06-27 |
| EP2861571B1 (en) | 2017-05-03 |
| CN104428292B (zh) | 2017-02-08 |
| JP2015531746A (ja) | 2015-11-05 |
| CN104428292A (zh) | 2015-03-18 |
| JP6001168B2 (ja) | 2016-10-05 |
| KR20150023393A (ko) | 2015-03-05 |
| US20150266848A1 (en) | 2015-09-24 |
| US9221783B2 (en) | 2015-12-29 |
| ES2635067T3 (es) | 2017-10-02 |
| KR101699145B1 (ko) | 2017-02-03 |
| WO2013187727A1 (en) | 2013-12-19 |
| CA2874988A1 (en) | 2013-12-19 |
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