BR112014031396B1 - composto de sulfamato de fenilalquila e composição de relaxante muscular compreendendo o mesmo - Google Patents

Info

Publication number

BR112014031396B1

BR112014031396B1 BR112014031396A BR112014031396A BR112014031396B1 BR 112014031396 B1 BR112014031396 B1 BR 112014031396B1 BR 112014031396 A BR112014031396 A BR 112014031396A BR 112014031396 A BR112014031396 A BR 112014031396A BR 112014031396 B1 BR112014031396 B1 BR 112014031396B1

Authority

BR

Brazil

Prior art keywords

methyl

preparation example

sulfamate

dioxolan

dioxaspiro

Prior art date

2012-06-15

Links

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• Global Dossier
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• -1 phenylalkyl sulfamate compound Chemical class 0.000 title claims abstract description 409
• 239000000203 mixture Substances 0.000 title claims abstract description 60
• 239000003158 myorelaxant agent Substances 0.000 title description 9
• 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 635
• FIYXUOWXHWJDAM-UHFFFAOYSA-N methyl sulfamate Chemical compound COS(N)(=O)=O FIYXUOWXHWJDAM-UHFFFAOYSA-N 0.000 claims description 97
• 239000000460 chlorine Substances 0.000 claims description 73
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 59
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 58
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 38
• 150000003839 salts Chemical class 0.000 claims description 28
• IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 claims description 25
• 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 22
• 239000002253 acid Substances 0.000 claims description 20
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
• 125000006304 2-iodophenyl group Chemical group [H]C1=C([H])C(I)=C(*)C([H])=C1[H] 0.000 claims description 14
• BGGQCYYULFFRLC-UHFFFAOYSA-N ethyl sulfamate Chemical compound CCOS(N)(=O)=O BGGQCYYULFFRLC-UHFFFAOYSA-N 0.000 claims description 14
• 229910052739 hydrogen Inorganic materials 0.000 claims description 14
• 239000001257 hydrogen Substances 0.000 claims description 14
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 13
• 238000006243 chemical reaction Methods 0.000 claims description 12
• 238000005906 dihydroxylation reaction Methods 0.000 claims description 9
• ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 claims description 8
• 229910052799 carbon Inorganic materials 0.000 claims description 8
• 239000003638 chemical reducing agent Substances 0.000 claims description 8
• 150000002431 hydrogen Chemical class 0.000 claims description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
• 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 description 6
• 125000000217 alkyl group Chemical group 0.000 claims description 6
• 239000007800 oxidant agent Substances 0.000 claims description 6
• 210000000278 spinal cord Anatomy 0.000 claims description 6
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 5
• 206010019196 Head injury Diseases 0.000 claims description 5
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 5
• 206010041415 Spastic paralysis Diseases 0.000 claims description 4
• 206010041591 Spinal osteoarthritis Diseases 0.000 claims description 4
• 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 description 4
• 125000003277 amino group Chemical group 0.000 claims description 4
• 125000003118 aryl group Chemical group 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
• 125000000753 cycloalkyl group Chemical group 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
• 125000006527 (C1-C5) alkyl group Chemical group 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
• 208000010112 Spinocerebellar Degenerations Diseases 0.000 claims description 3
• 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 description 3
• 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 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
• 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 2
• 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
• 206010033799 Paralysis Diseases 0.000 claims description 2
• 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 description 2
• 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 description 2
• SIUKEWDCAFMXPT-UHFFFAOYSA-N [3-(2-iodophenyl)-1,4-dioxaspiro[4.4]nonan-2-yl]methyl sulfamate Chemical compound S(N)(OCC1OC2(OC1C1=C(C=CC=C1)I)CCCC2)(=O)=O SIUKEWDCAFMXPT-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 239000004480 active ingredient Substances 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
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
• 230000001148 spastic effect Effects 0.000 claims description 2
• 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
• 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
• 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
• 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
• 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
• GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 1
• 230000000694 effects Effects 0.000 abstract description 20
• 210000003205 muscle Anatomy 0.000 abstract description 7
• 238000002360 preparation method Methods 0.000 description 1255
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 594
• 238000005481 NMR spectroscopy Methods 0.000 description 539
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 493
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 154
• CSXVIDKEWQWVHS-GHMZBOCLSA-N [(4r,5r)-5-(2-chlorophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol Chemical compound O1C(C)(C)O[C@H](CO)[C@H]1C1=CC=CC=C1Cl CSXVIDKEWQWVHS-GHMZBOCLSA-N 0.000 description 136
• BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 102
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 82
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 79
• 229950010765 pivalate Drugs 0.000 description 74
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 72
• IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 53
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 48
• 239000000243 solution Substances 0.000 description 46
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
• 229910001868 water Inorganic materials 0.000 description 46
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 43
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 41
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 40
• 235000019439 ethyl acetate Nutrition 0.000 description 39
• FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 38
• 239000011541 reaction mixture Substances 0.000 description 34
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 30
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 30
• 239000000741 silica gel Substances 0.000 description 30
• 229910002027 silica gel Inorganic materials 0.000 description 30
• 238000012360 testing method Methods 0.000 description 30
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 28
• 125000001309 chloro group Chemical group Cl* 0.000 description 22
• 239000012044 organic layer Substances 0.000 description 20
• 239000010410 layer Substances 0.000 description 17
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 17
• 235000019341 magnesium sulphate Nutrition 0.000 description 17
• YOQYREMLLOVQAA-BDAKNGLRSA-N methyl (2s,3r)-3-(2-chlorophenyl)-2,3-dihydroxypropanoate Chemical compound COC(=O)[C@@H](O)[C@H](O)C1=CC=CC=C1Cl YOQYREMLLOVQAA-BDAKNGLRSA-N 0.000 description 17
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 17
• 241000699670 Mus sp. Species 0.000 description 15
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• GIMWJHKHFHUKMY-WDEREUQCSA-N methyl (4R,5S)-5-(2-chlorophenyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate Chemical compound ClC1=C(C=CC=C1)[C@H]1[C@@H](OC(O1)(C)C)C(=O)OC GIMWJHKHFHUKMY-WDEREUQCSA-N 0.000 description 15
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 14
• QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 14
• SAOSCTYRONNFTC-UHFFFAOYSA-N 2-methyl-decanoic acid Chemical compound CCCCCCCCC(C)C(O)=O SAOSCTYRONNFTC-UHFFFAOYSA-N 0.000 description 13
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 13
• YOQYREMLLOVQAA-DTWKUNHWSA-N methyl (2r,3s)-3-(2-chlorophenyl)-2,3-dihydroxypropanoate Chemical compound COC(=O)[C@H](O)[C@@H](O)C1=CC=CC=C1Cl YOQYREMLLOVQAA-DTWKUNHWSA-N 0.000 description 12
• SBVWZRBKTDOSDR-GQCTYLIASA-N 1-chloro-2-[(e)-3-(methoxymethoxy)prop-1-enyl]benzene Chemical compound COCOC\C=C\C1=CC=CC=C1Cl SBVWZRBKTDOSDR-GQCTYLIASA-N 0.000 description 11
• KUSYIGBGHPOWEL-UHFFFAOYSA-N 2-methyl nonaoic acid Chemical compound CCCCCCCC(C)C(O)=O KUSYIGBGHPOWEL-UHFFFAOYSA-N 0.000 description 11
• FGTHJSRVJADEHH-OLZOCXBDSA-N methyl (4s,5r)-5-(2-chlorophenyl)-2,2-diethyl-1,3-dioxolane-4-carboxylate Chemical compound O1C(CC)(CC)O[C@H](C(=O)OC)[C@H]1C1=CC=CC=C1Cl FGTHJSRVJADEHH-OLZOCXBDSA-N 0.000 description 11
• 239000008194 pharmaceutical composition Substances 0.000 description 11
• 125000000068 chlorophenyl group Chemical group 0.000 description 10
• UBHZUDXTHNMNLD-UHFFFAOYSA-N dimethylsilane Chemical compound C[SiH2]C UBHZUDXTHNMNLD-UHFFFAOYSA-N 0.000 description 10
• ADJSTZGNQDCVHW-RFSDDRETSA-N methyl (4s,5r)-5-(2-iodophenyl)-2-methyl-1,3-dioxolane-4-carboxylate Chemical compound COC(=O)[C@H]1OC(C)O[C@@H]1C1=CC=CC=C1I ADJSTZGNQDCVHW-RFSDDRETSA-N 0.000 description 10
• NNZPTXZGXIGYGW-JXMROGBWSA-N tert-butyl-dimethyl-[(e)-5-phenylpent-3-enoxy]silane Chemical compound CC(C)(C)[Si](C)(C)OCC\C=C\CC1=CC=CC=C1 NNZPTXZGXIGYGW-JXMROGBWSA-N 0.000 description 10
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 9
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
• PPMVXZLGSOOHNV-QWRGUYRKSA-N [(4S,5S)-5-(2-aminophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound CC1(C)O[C@@H](COS(N)(=O)=O)[C@@H](O1)C1=C(N)C=CC=C1 PPMVXZLGSOOHNV-QWRGUYRKSA-N 0.000 description 8
• 239000012043 crude product Substances 0.000 description 8
• POTRTUQCRHOIFM-VOTSOKGWSA-N methyl (e)-3-(2-chlorophenyl)prop-2-enoate Chemical compound COC(=O)\C=C\C1=CC=CC=C1Cl POTRTUQCRHOIFM-VOTSOKGWSA-N 0.000 description 8
• DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 8
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
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• RZMCTLKVIWUBPA-GHMZBOCLSA-N [(4r,5r)-5-(2-chlorophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl sulfamate Chemical compound O1C(C)(C)O[C@H](COS(N)(=O)=O)[C@H]1C1=CC=CC=C1Cl RZMCTLKVIWUBPA-GHMZBOCLSA-N 0.000 description 3
• KCIYNTMFUNIJHH-GHMZBOCLSA-N [(4r,5r)-5-(2-fluorophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol Chemical compound O1C(C)(C)O[C@H](CO)[C@H]1C1=CC=CC=C1F KCIYNTMFUNIJHH-GHMZBOCLSA-N 0.000 description 3
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• KKXUEHPFMXQOBO-UHFFFAOYSA-N [1-(2-chlorophenyl)-1-hydroxy-3-phenylmethoxypropan-2-yl] acetate Chemical compound C=1C=CC=C(Cl)C=1C(O)C(OC(=O)C)COCC1=CC=CC=C1 KKXUEHPFMXQOBO-UHFFFAOYSA-N 0.000 description 3
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• 230000015572 biosynthetic process Effects 0.000 description 3
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• 230000006378 damage Effects 0.000 description 3
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• LWZSTWUMLQVWOV-VHSXEESVSA-N ethyl (2r,3s)-3-(2,6-dichlorophenyl)-2,3-dihydroxypropanoate Chemical compound CCOC(=O)[C@H](O)[C@@H](O)C1=C(Cl)C=CC=C1Cl LWZSTWUMLQVWOV-VHSXEESVSA-N 0.000 description 3
• LWZSTWUMLQVWOV-ZJUUUORDSA-N ethyl (2s,3r)-3-(2,6-dichlorophenyl)-2,3-dihydroxypropanoate Chemical compound CCOC(=O)[C@@H](O)[C@H](O)C1=C(Cl)C=CC=C1Cl LWZSTWUMLQVWOV-ZJUUUORDSA-N 0.000 description 3
• JAKOHGXFAISIIX-BMVHATROSA-N ethyl (4s,5r)-5-(2,6-dichlorophenyl)-2-methyl-1,3-dioxolane-4-carboxylate Chemical compound CCOC(=O)[C@H]1OC(C)O[C@@H]1C1=C(Cl)C=CC=C1Cl JAKOHGXFAISIIX-BMVHATROSA-N 0.000 description 3
• LUUHRZVWQLCAAC-VOTSOKGWSA-N ethyl (e)-3-(2,6-dichlorophenyl)prop-2-enoate Chemical compound CCOC(=O)\C=C\C1=C(Cl)C=CC=C1Cl LUUHRZVWQLCAAC-VOTSOKGWSA-N 0.000 description 3
• 210000003414 extremity Anatomy 0.000 description 3
• 125000001207 fluorophenyl group Chemical group 0.000 description 3
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• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
• 231100000053 low toxicity Toxicity 0.000 description 3
• NPSNZGXOMWNEAS-OLZOCXBDSA-N methyl (2R,3S)-2-(2-chlorophenyl)-1,4-dioxaspiro[4.4]nonane-3-carboxylate Chemical compound COC(=O)[C@H]1OC2(O[C@@H]1C1=C(C=CC=C1)Cl)CCCC2 NPSNZGXOMWNEAS-OLZOCXBDSA-N 0.000 description 3
• PKIHMXNDXQQKLV-KGLIPLIRSA-N methyl (2R,3S)-2-(2-chlorophenyl)-1,4-dioxaspiro[4.5]decane-3-carboxylate Chemical compound COC(=O)[C@H]1OC2(O[C@@H]1C1=C(C=CC=C1)Cl)CCCCC2 PKIHMXNDXQQKLV-KGLIPLIRSA-N 0.000 description 3
• NADDFKGRMPCCIK-OLZOCXBDSA-N methyl (2R,3S)-2-(2-nitrophenyl)-1,4-dioxaspiro[4.4]nonane-3-carboxylate Chemical compound COC(=O)[C@H]1OC2(O[C@@H]1C1=C(C=CC=C1)[N+](=O)[O-])CCCC2 NADDFKGRMPCCIK-OLZOCXBDSA-N 0.000 description 3
• PKIHMXNDXQQKLV-UONOGXRCSA-N methyl (2S,3R)-2-(2-chlorophenyl)-1,4-dioxaspiro[4.5]decane-3-carboxylate Chemical compound COC(=O)[C@@H]1OC2(O[C@H]1C1=C(C=CC=C1)Cl)CCCCC2 PKIHMXNDXQQKLV-UONOGXRCSA-N 0.000 description 3
• SHLVTZUCOHMDFB-UONOGXRCSA-N methyl (2S,3R)-2-(2-fluorophenyl)-1,4-dioxaspiro[4.5]decane-3-carboxylate Chemical compound COC(=O)[C@@H]1OC2(O[C@H]1C1=C(C=CC=C1)F)CCCCC2 SHLVTZUCOHMDFB-UONOGXRCSA-N 0.000 description 3
• LHRVKMVLVYDRIA-LSDHHAIUSA-N methyl (2S,3R)-2-[(2-chlorophenyl)methyl]-1,4-dioxaspiro[4.5]decane-3-carboxylate Chemical compound COC(=O)[C@@H]1OC2(O[C@H]1CC1=C(C=CC=C1)Cl)CCCCC2 LHRVKMVLVYDRIA-LSDHHAIUSA-N 0.000 description 3
• RVPRPDNJVHSZMP-VHSXEESVSA-N methyl (2r,3s)-2,3-dihydroxy-3-(2-methylphenyl)propanoate Chemical compound COC(=O)[C@H](O)[C@@H](O)C1=CC=CC=C1C RVPRPDNJVHSZMP-VHSXEESVSA-N 0.000 description 3
• WDEHOPIDTGUFDP-DTWKUNHWSA-N methyl (2r,3s)-3-(2,4-dichlorophenyl)-2,3-dihydroxypropanoate Chemical compound COC(=O)[C@H](O)[C@@H](O)C1=CC=C(Cl)C=C1Cl WDEHOPIDTGUFDP-DTWKUNHWSA-N 0.000 description 3
• MIGDMMVNXISYOC-BDAKNGLRSA-N methyl (2s,3r)-2,3-dihydroxy-3-(2-iodophenyl)propanoate Chemical compound COC(=O)[C@@H](O)[C@H](O)C1=CC=CC=C1I MIGDMMVNXISYOC-BDAKNGLRSA-N 0.000 description 3
• IXDRYSIPXMREGK-BDAKNGLRSA-N methyl (2s,3r)-2,3-dihydroxy-3-phenylpropanoate Chemical compound COC(=O)[C@@H](O)[C@H](O)C1=CC=CC=C1 IXDRYSIPXMREGK-BDAKNGLRSA-N 0.000 description 3
• FVZVGQXENGKWNR-OLZOCXBDSA-N methyl (4S,5R)-2,2-diethyl-5-phenyl-1,3-dioxolane-4-carboxylate Chemical compound COC(=O)[C@H]1OC(O[C@@H]1C1=CC=CC=C1)(CC)CC FVZVGQXENGKWNR-OLZOCXBDSA-N 0.000 description 3
• FGTHJSRVJADEHH-QWHCGFSZSA-N methyl (4r,5s)-5-(2-chlorophenyl)-2,2-diethyl-1,3-dioxolane-4-carboxylate Chemical compound O1C(CC)(CC)O[C@@H](C(=O)OC)[C@@H]1C1=CC=CC=C1Cl FGTHJSRVJADEHH-QWHCGFSZSA-N 0.000 description 3
• BJIFYZSPIGVZPX-KGLIPLIRSA-N methyl (4s,5r)-2,2-diethyl-5-(2-methylphenyl)-1,3-dioxolane-4-carboxylate Chemical compound O1C(CC)(CC)O[C@H](C(=O)OC)[C@H]1C1=CC=CC=C1C BJIFYZSPIGVZPX-KGLIPLIRSA-N 0.000 description 3
• IQWZZFZVDBWCGY-OLZOCXBDSA-N methyl (4s,5r)-2,2-diethyl-5-(2-nitrophenyl)-1,3-dioxolane-4-carboxylate Chemical compound O1C(CC)(CC)O[C@H](C(=O)OC)[C@H]1C1=CC=CC=C1[N+]([O-])=O IQWZZFZVDBWCGY-OLZOCXBDSA-N 0.000 description 3
• VMGNKMMEEIELCN-QZNDUUOJSA-N methyl (4s,5r)-2-methyl-5-(2-methylphenyl)-1,3-dioxolane-4-carboxylate Chemical compound COC(=O)[C@H]1OC(C)O[C@@H]1C1=CC=CC=C1C VMGNKMMEEIELCN-QZNDUUOJSA-N 0.000 description 3
• BEIHBSZGYLFXIV-OLZOCXBDSA-N methyl (4s,5r)-5-(2,4-dichlorophenyl)-2,2-diethyl-1,3-dioxolane-4-carboxylate Chemical compound O1C(CC)(CC)O[C@H](C(=O)OC)[C@H]1C1=CC=C(Cl)C=C1Cl BEIHBSZGYLFXIV-OLZOCXBDSA-N 0.000 description 3
• GIMWJHKHFHUKMY-MNOVXSKESA-N methyl (4s,5r)-5-(2-chlorophenyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate Chemical compound COC(=O)[C@H]1OC(C)(C)O[C@@H]1C1=CC=CC=C1Cl GIMWJHKHFHUKMY-MNOVXSKESA-N 0.000 description 3
• HEGMSNMENPDWJB-VOTSOKGWSA-N methyl (e)-3-(2-fluorophenyl)prop-2-enoate Chemical compound COC(=O)\C=C\C1=CC=CC=C1F HEGMSNMENPDWJB-VOTSOKGWSA-N 0.000 description 3
• XPRREVLGOYVUEZ-UHFFFAOYSA-N methyl 2-methyl-5-(2-nitrophenyl)-1,3-dioxolane-4-carboxylate Chemical compound COC(=O)C1OC(C)OC1c1ccccc1[N+]([O-])=O XPRREVLGOYVUEZ-UHFFFAOYSA-N 0.000 description 3
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• GRLUWXQRNMHDRW-QWHCGFSZSA-N methyl (2s,3r)-2-(2,4-dichlorophenyl)-1,4-dioxaspiro[4.4]nonane-3-carboxylate Chemical compound O([C@H]([C@@H](O1)C=2C(=CC(Cl)=CC=2)Cl)C(=O)OC)C21CCCC2 GRLUWXQRNMHDRW-QWHCGFSZSA-N 0.000 description 1
• ZKSRWCKXTJYKFO-QWHCGFSZSA-N methyl (2s,3r)-2-(2-iodophenyl)-1,4-dioxaspiro[4.4]nonane-3-carboxylate Chemical compound O([C@H]([C@@H](O1)C=2C(=CC=CC=2)I)C(=O)OC)C21CCCC2 ZKSRWCKXTJYKFO-QWHCGFSZSA-N 0.000 description 1
• VJLQHJGRBJZEPE-QWHCGFSZSA-N methyl (4R,5S)-2,2-diethyl-5-(2-iodophenyl)-1,3-dioxolane-4-carboxylate Chemical compound COC(=O)[C@@H]1OC(O[C@H]1C1=C(C=CC=C1)I)(CC)CC VJLQHJGRBJZEPE-QWHCGFSZSA-N 0.000 description 1
• MHTRELQZDRVZRV-WDEREUQCSA-N methyl (4R,5S)-5-(2,4-dichlorophenyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate Chemical compound COC(=O)[C@@H]1OC(O[C@H]1C1=C(C=C(C=C1)Cl)Cl)(C)C MHTRELQZDRVZRV-WDEREUQCSA-N 0.000 description 1
• BBUHAKFAFBXHQI-SWQDIRLTSA-N methyl (4R,5S)-5-(2-methylphenyl)-2-phenyl-1,3-dioxolane-4-carboxylate Chemical compound COC(=O)[C@@H]1OC(O[C@H]1C1=C(C=CC=C1)C)C1=CC=CC=C1 BBUHAKFAFBXHQI-SWQDIRLTSA-N 0.000 description 1
• OYUFGBRNGOELFL-UONOGXRCSA-N methyl (4R,5S)-5-[(2-chlorophenyl)methyl]-2,2-diethyl-1,3-dioxolane-4-carboxylate Chemical compound COC(=O)[C@@H]1OC(O[C@H]1CC1=C(C=CC=C1)Cl)(CC)CC OYUFGBRNGOELFL-UONOGXRCSA-N 0.000 description 1
• SNPBPXKTDWIBLM-RFSDDRETSA-N methyl (4S,5R)-5-(2-chlorophenyl)-2-methyl-1,3-dioxolane-4-carboxylate Chemical compound COC(=O)[C@H]1OC(O[C@@H]1C1=C(C=CC=C1)Cl)C SNPBPXKTDWIBLM-RFSDDRETSA-N 0.000 description 1
• QNTMWERQDNQBBZ-RFSDDRETSA-N methyl (4S,5R)-5-(2-fluorophenyl)-2-methyl-1,3-dioxolane-4-carboxylate Chemical compound COC(=O)[C@H]1OC(O[C@@H]1C1=C(C=CC=C1)F)C QNTMWERQDNQBBZ-RFSDDRETSA-N 0.000 description 1
• BBUHAKFAFBXHQI-LNKXUWQBSA-N methyl (4S,5R)-5-(2-methylphenyl)-2-phenyl-1,3-dioxolane-4-carboxylate Chemical compound COC(=O)[C@H]1OC(O[C@@H]1C1=C(C=CC=C1)C)C1=CC=CC=C1 BBUHAKFAFBXHQI-LNKXUWQBSA-N 0.000 description 1
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• BJIFYZSPIGVZPX-UONOGXRCSA-N methyl (4r,5s)-2,2-diethyl-5-(2-methylphenyl)-1,3-dioxolane-4-carboxylate Chemical compound O1C(CC)(CC)O[C@@H](C(=O)OC)[C@@H]1C1=CC=CC=C1C BJIFYZSPIGVZPX-UONOGXRCSA-N 0.000 description 1
• XPRREVLGOYVUEZ-ZJVIIBSASA-N methyl (4r,5s)-2-methyl-5-(2-nitrophenyl)-1,3-dioxolane-4-carboxylate Chemical compound COC(=O)[C@@H]1OC(C)O[C@H]1C1=CC=CC=C1[N+]([O-])=O XPRREVLGOYVUEZ-ZJVIIBSASA-N 0.000 description 1
• BEIHBSZGYLFXIV-QWHCGFSZSA-N methyl (4r,5s)-5-(2,4-dichlorophenyl)-2,2-diethyl-1,3-dioxolane-4-carboxylate Chemical compound O1C(CC)(CC)O[C@@H](C(=O)OC)[C@@H]1C1=CC=C(Cl)C=C1Cl BEIHBSZGYLFXIV-QWHCGFSZSA-N 0.000 description 1
• WROYTTWEGQXTGK-YAPKUGLOSA-N methyl (4r,5s)-5-(2,4-dichlorophenyl)-2-methyl-1,3-dioxolane-4-carboxylate Chemical compound COC(=O)[C@@H]1OC(C)O[C@H]1C1=CC=C(Cl)C=C1Cl WROYTTWEGQXTGK-YAPKUGLOSA-N 0.000 description 1
• VJLQHJGRBJZEPE-OLZOCXBDSA-N methyl (4s,5r)-2,2-diethyl-5-(2-iodophenyl)-1,3-dioxolane-4-carboxylate Chemical compound O1C(CC)(CC)O[C@H](C(=O)OC)[C@H]1C1=CC=CC=C1I VJLQHJGRBJZEPE-OLZOCXBDSA-N 0.000 description 1
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